CADERNO DE

QUMICA ORGNICA EXPERIMENTAL

2a Edio revista e atualizada

Dmaris Silveira

Professora Titular do
Centro de Cincias Exatas e Tecnolgicas da
Universidade Vale do Rio Doce - UNIVALE

Governador Valadares/Minas Gerais

2001

UNIVERSIDADE VALE DO RIO DOCE

Reitor
Hermrio Gomes da Silva
Pr-Reitora Acadmica
Maria Alice Lima Graciolli Fraga de Assis

Catalogao: Biblioteca Central da UNIVALE

Bibliotecria responsvel: Elizabete Karakedo Figueiredo
Silveira, Dmaris
Qumica Orgnica Experimental/
Dmaris Silveira Duarte. 2. ed.
Governador Valadares/MG: UNIVALE,
2001
p: il.
UNIVALE; n. 1

(Cadernos

Acadmicos

1. Qumica Orgnica. I. Ttulo. II. Srie.

CDU 547(076.5)

INTRODUO
Este livro destina-se aos estudantes de graduao em Qumica, Farmcia e outros cursos que incluam aulas prticas ou
disciplinas experimentais de Qumica Orgnica. Foi organizado para suprir uma carncia que existe quanto a manuais de Qumica
Orgnica Experimental, na lngua portuguesa. Mais especificamente, para a utilizao nas aulas das disciplinas Qumica Orgnica e
Qumica Orgnica Experimental, da Universidade Vale do Rio Doce.
Apesar da Qumica Orgnica ter passado, nos ltimos anos, por um grande desenvolvimento, muitos dos conceitos,
mtodos de sntese e de anlise que so encontrados nos livros-texto, so difceis de serem demonstrados ou executados em
laboratrio, devido enorme dificuldade, encontrada pela maioria das instituies de ensino, para adequar e modernizar os
laboratrios de Qumica.
Assim, foram escolhidos 21 experimentos clssicos de sntese, separao e purificao de compostos orgnicos, com o
objetivo de ilustrar o contedo terico da disciplina Qumica Orgnica. Os experimentos descritos podem ser realizados com
reagentes e equipamentos facilmente encontrados em um laboratrio que possua uma infra-estrutura mnima. Todos os experimentos
foram testados, podendo ser realizados com segurana.
Antes de cada experimento, o estudante deve preparar-se, realizando uma reviso terica sobre o assunto a ser abordado.
Para isto, so includas algumas questes que devem ser respondidas antes, durante e depois da aula prtica, que auxiliaro no
entendimento da aula.
Durante o curso, devem ser realizados seminrios e estudos dirigidos que complementaro o aprendizado, fortalecendo a
base terica em Qumica Orgnica e revendo os conceitos de Qumica Geral.
O objetivo essencial consiste em levar os estudantes a apreender e exercitar uma metodologia de trabalho, aprender a
pensar e decidir, bem como assumir atitudes responsveis, consigo mesmo e com seus colegas.

Governador Valadares, fevereiro de 2000

A autora

MAS POUCAS PALAVRAS INTRODUTRIAS

Antes de iniciar o Curso de Qumica Orgnica Experimental, importante que voc leia as pginas seguintes, que trazem
orientaes e informaes que sero teis, no s durante as aulas, mas tambm durante sua vida profissional. E se, em qualquer
momento, surgir alguma dvida, no hesite em reler estas instrues ou perguntar ao seu professor.

SEGURANA: ANTES, DURANTE E SEMPRE!!

O laboratrio de Qumica Orgnica um dos mais perigosos entre aqueles utilizados por estudantes de graduao. Uma
longa lista de dvidas sobre o procedimento do estudante durante as aulas e/ou a execuo de um experimento geralmente aparece
durante ano letivo. Devido a isto, existe uma srie de normas de segurana que devem ser seguidas por todos: estudantes,
professores, monitores, tcnicos e estagirios. O castigo para quem no obedece estas regras simples muito real! Pode levar a
muito sofrimento para quem no as seguiu e para quem est ao redor.
UM RECADO PARA VOC: Tudo bem, se voc acha que tudo isto um monte de bobagens com o intuito de assustar...
voc pode at ignorar estas regras. Mas lembre-se...

VOC FOI AVISADO!

1)

Quando devo utilizar culos de segurana?

Qualquer injria ocular extremamente sria e muitas vezes irreversvel. Mas pode ser prevenida se voc utilizar os
culos de segurana durante todo o tempo que estiver realizando um experimento. Os culos de segurana podem ser deselegantes,
incmodos e pesados, mas realmente protegem de gases, respingos de cidos ou solventes.
2) Posso tocar meus olhos e boca durante os experimentos?
De forma alguma! Nem durante os experimentos, nem em qualquer momento que voc estiver dentro do laboratrio! No
toque seu rosto, brao, boca ou qualquer parte do seu corpo, sem antes lavar e muito bem suas mos.
Muitas vezes a bancada, ou qualquer material, est contaminada com algum reagente que voc no consegue detectar,
pois sua concentrao baixa ou estava sob a forma lquida e, no momento, est seco. Mas o perigo ainda est l!
3) Posso dispor do material utilizado (papel de filtro usado, papel indicador de pH, resduos slidos ou
lquidos) da mesma forma e no mesmo lugar que outros materiais?
A eliminao de lixo qumico um grande problema! Se voc o joga fora, da mesma forma que voc faz com o lixo
domstico, por exemplo, certamente este lixo vai envenenar algum mais frente. Sempre pergunte ao seu professor, se voc tiver
qualquer dvida quanto a isto.
Todo material produzido deve ser corretamente rotulado. Quando houver rtulos danificados ou ilegveis, devem ser
imediatamente substitudos.
4) Posso trabalhar sozinho?
Voc nunca deve trabalhar sozinho! Se houver algum acidente, enquanto est sozinho, de tal gravidade que voc no
esteja em condies de resolv-lo, voc estar com um graaande problema!
5) Posso me divertir dentro do laboratrio?
Os experimentos de Qumica Orgnica podem ser muito agradveis, mas so um negcio muito srio! No se distraia ou
fique brincando pelo laboratrio. Voc pode prejudicar a si mesmo ou ao seu colega. Seja responsvel com sua vida e com a do
outro!
6) Que trabalho defensivo no laboratrio de Qumica?
Significa trabalhar como se algum mais fosse sofrer um acidente que pode lhe afetar. Assim, utilize os culos de
proteo porque algum pode estar com um tubo de ensaio contendo algo em ebulio, apontado para seu rosto. Utilize o jaleco,
pois algum pode espirrar algum liquido quente, cido concentrado ou solventes em seu corpo.
7) Ao final do trabalho, como devo proceder?
Deixe tudo limpo: sua rea de trabalho limpa e seca; a vidraria utilizada lavada ou, se no for possvel, depositada em
local adequado; o lixo depositado no local adequado. Feche todas as torneiras de gs e gua. Deixe os frascos com as tampas bem
arrolhadas. Deixe a capela desligada e limpa.
8) Posso comer, beber ou fumar no laboratrio?
Voc est brincando??!! Quer morrer envenenado ou explodir, quando acender seu cigarro????!!!!
9) O laboratrio possui equipamento de segurana?
Sim, e voc deve aprender onde esto localizados e qual a maneira correta de utilizao dos extintores de incndio,
chuveiros e lava-olhos.
Todo laboratrio deve estar equipado com uma caixa de primeiros socorros, mantida em local de fcil acesso. Esta caixa
deve conter, ao menos, os seguintes artigos:

leo mineral

Pomada para queimaduras

Soluo aquosa de cido actico a 1%

Soluo aquosa de cido brico a 1%

Soluo aquosa de bicarbonato de sdio a 1%

Etanol, glicerina, soro fisiolgico

Gaze, esparadrapo

Mercuro-cromo, tintura de iodo.

Conserve a caixa de primeiros socorros. Um dia talvez voc necessite utiliz-la.
10) H realmente necessidade de estar sempre de jaleco?
Mantenha-se sempre, independente do calor, coberto da cabea aos ps. No trabalhe com bermudas, mini-blusas, minisaias (ou qualquer outra coisa mini). Evite estar de chinelos ou sapatos de pano. Isto lhe parece muito desconfortvel?! Ento
pense como seria carregar consigo uma queimadura qumica nos ps; ou uma cicatriz em sua barriga ou brao... Dependendo do
experimento, no descarte o uso de luvas.

Mantenha os cabelos longos amarrados. Voc no quer que eles queimem ou encostem dentro de um bquer contendo
cido.
Lembre-se: Voc no poder freqentar a aula sem o jaleco.
11) Como fazer quando houver necessidade de aquecer algo?
Os experimentos de qumica orgnica geralmente so realizados com solventes inflamveis. CUIDADO!! Cheque todo o
material que voc vai utilizar. S utilize bico de gs quando orientado pelo professor.
12) Para que serve a capela?
A capela um local de trabalho contendo, ao menos, um exaustor que retira gases do ambiente. A porta transparente
serve para a proteo contra gases, respingos e exploses. Se possvel, considere toda substncia qumica (slidos, lquidos e gases)
como se fossem txicas e trabalhe sempre na capela.
13) Devo sempre esperar o professor me dizer o que fazer?
No incio da aula, provavelmente voc estar com seu roteiro de prtica (que voc dever ter lido antes) e o professor
dar mais orientaes sobre o experimento, quanto a detalhes, segurana, etc. Preste muita ateno e faa todas as perguntas que
queira. No existe dvida boba. O que voc no sabe, pode lhe ferir. Seja responsvel com voc mesmo e com sua aprendizagem.
Durante o experimento, mantenha seu roteiro e seu caderno sempre mo, seguindo-o atentamente.
14) Que fazer se ocorrer um acidente?
Se voc se cortar e no for srio, lave o ferimento com gua.; se houver muito sangramento, pressione o local e solicite
ajuda. Se voc se queimar levemente, deixe cair gua fria sobre o local. Mas se for queimadura qumica, notifique o professor
IMEDIATAMENTE!
15) Tenho plena liberdade dentro do laboratrio?
Todo o material e reagentes necessrios para a aula prtica estaro em seu local de trabalho. Se houver necessidade de
mais alguma coisa, pea ao professor e ao monitor. Voc no deve entrar na rea de estocagem . Tambm, para sua segurana, no
permitido realizar qualquer experimento sem prvia autorizao.
16) E se eu ficar grvida? Como devo proceder?
Notifique ao seu professor. Muitos solventes e reagentes utilizados nas aulas prticas de Qumica Orgnica so txicos e
podem prejudicar voc e ao seu beb. Seu professor a pessoa mais indicada para lhe orientar quanto segurana.

ORGANIZAO DO CADERNO E ELABORAO DOS RELATRIOS

O caderno de laboratrio uma ferramenta extremamente til, se for bem organizado. uma fonte de informaes para
que voc possa fazer seu relatrio, bem como consultar, em caso de dvidas posteriores. Folhas soltas acabam sendo perdidas
juntamente com anotaes valiosas. Algumas dicas para mant-lo:
1)
2)
3)
4)

Trate seu caderno como um confidente: anote o que VOC fez durante a aula, muito mais do que o que foi dito pelo professor.
Sempre utilize lpis. Tinta de caneta pode manchar com gua ou certos tipos de solventes.
Anote toda e qualquer observao: mudanas de cor, temperatura, exploso e qualquer explicao para ter acontecido o que
aconteceu.
Anote todo o material e reagentes que voc utilizar durante o experimento. Se possvel, inclua algumas caractersticas tais
como, peso molecular, ponto de ebulio, densidade, etc.

Quanto ao experimento que voc vai realizar, este pode ser, basicamente, de duas naturezas: um experimento tcnico ou
um experimento de sntese. Para cada um h uma abordagem diferente.
A)

1)
2)
B)
1)
2)
3)
4)
5)

O EXPERIMENTO TCNICO: realizado para que voc pratique uma certa operao antes que a utilize, como uma
ferramenta, em outros experimentos. Por exemplo, a destilao de uma mistura um experimento tcnico tpico. Voc a
utilizar em vrios outros experimentos.
Leia a descrio e os princpios tericos da tcnica bem como as operaes envolvidas. Escreva em seu caderno um resumo,
ressaltando os pontos importantes. Este resumo pode servir como base para a introduo do seu relatrio.
Planeje toda a experincia a ser executada e, se possvel, inclua o desenho da aparelhagem.
O EXPERIMENTO DE SNTESE: o objetivo , partindo de um substrato adequado, preparar uma amostra purificada do
produto que voc deseja.
Leia todo o roteiro e os conceitos tericos envolvidos na reao, procurando ampliar seus conhecimentos em outros textos.
Anote a equao referente reao a ser executada , bem como o mecanismo envolvido.
Anote constantes fsicas, toxicidade e os cuidados necessrios para a manipulao dos reagentes.
Calcule o rendimento terico da reao.
Ao final do experimento, calcule o rendimento da reao em porcentagem.

Se voc ainda tem dvidas da importncia do seu caderno de

laboratrio, faa estas perguntas a si mesmo:
1)
Antes da aula: Posso realizar o experimento sem qualquer manual de
laboratrio?
2)
IMEDIATAMENTE depois da aula (no mais tarde): Se no houvesse
qualquer outro texto, eu poderia duplicar os resultados, s utilizando minhas
anotaes?

1)
2)
3)

Quanto ao relatrio, este dever conter os seguintes itens:

Ttulo da experincia.
Nome dos integrantes do grupo.
Introduo: descrevendo sucintamente a metodologia utilizada, caractersticas dos reagentes e produtos., etc.

4)
5)
6)
7)
8)

Material e reagentes: este item no imprescindvel, pois estar listado em seu roteiro de prtica e provavelmente voc
tambm j anotou em seu caderno.
Procedimento: NO COPIE DO SEU ROTEIRO! Descreva o que voc viu, o que voc fez e o que aconteceu.
Resultados: descreva cores formadas, resultados de testes de identificao, etc. Fornea os clculos estequiomtricos (se for
sntese) .
Discusso e concluso.
Referncias Bibliogrficas: de acordo com a ABNT.

AUXLIOS QUE SO BEM-VINDOS!

Voc deve se informar sobre qualquer reagente com o qual voc vai trabalhar. Informaes do tipo peso molecular,
densidade, solubilidade, estado fsico, pontos de fuso e ebulio, cor, toxicidade, etc. so imprescindveis para que voc possa
trabalhar com mais eficincia e responsabilidade.
Estes dados podem ser encontrados em sites relacionados com Qumica, na INTERNET, bem como em catlogos, que
podem ser solicitados para consulta, no prprio laboratrio ou na biblioteca.
s vezes no fcil consultar estes catlogos. Geralmente h necessidade de um conhecimento bsico da lngua inglesa,
mas com um pouco de prtica, possvel ganhar muito tempo com uma simples consulta.
Alguns exemplos:
CRC Handbook: um livro clssico, sempre atualizado, que traz tabelas contendo o nome, sinnimo e frmula dos compostos,
bem como PM, cor, forma cristalina, rotao especfica, absorbncia, PF, PE, densidade, solubilidade, etc.
LANGES: tambm clssico, traz basicamente as mesmas informaes que o CRC, tambm em forma de tabelas.
MERCK INDEX: traz informaes sobre frmacos e seus efeitos fisiolgicos, alm de trazer as constantes fsicas. Ao invs de
tabelas, as informaes so fornecidas sob a forma de textos.
CATLOGO ALDRICH: no um livro de referncia tradicional, mas relaciona vrias substncias, algumas ainda no
listadas nos catlogos tradicionais, fornecendo suas frmulas estruturais e as constantes fsicas .
Quanto Internet, se voc utilizar uma ferramenta de busca (Altavista, Yahoo, Excite, Cad, etc.) encontrar milhares de
sites relacionados Qumica. Infelizmente para aqueles que fogem da lngua inglesa, nesta lngua que ainda se encontram os
melhores sites e os mais completos bancos de dados.
Alguns sites interessantes e que podem ser acessados sem encargos:
1) http://www.sbq.org.br: homepage da Sociedade Brasileira de Qumica. uma pgina com atualizaes peridicas, onde voc
vai encontrar informaes sobre a SBQ e eventos, fatos interessantes em todas as reas da Qumica, links para outras pginas
de interesse, ferramenta de busca ,etc.
2) http://www.spq.pt: homepage da Sociedade Portuguesa de Qumica. Traz informaes sobre a SPQ, sobre eventos e alguns
textos interessantes.
3) http://www.chemicalonline.com: revista virtual, que, alm de artigos cientficos, traz tambm novidades da Qumica e links
para outras pginas interessantes.
4) http://www.drugsdiscoveryonline.com: revista virtual, com informaes sobre medicamentos.
5) http://chemweb.com: possui um banco de dados de propriedades de compostos orgnicos. Desta pgina, voc pode acessar ,
sem encargos, o Beilstein, uma ferramenta de busca para referncias bibliogrficas.
6) http://chemfinder.com: banco de dados que fornece as propriedades e a frmula estrutural dos compostos orgnicos.
7) http://www.chemclub.com: cadastrando-se neste clube virtual, voc poder ter acesso a uma srie de outras pginas
interessantes.
8) http://helium.dq.fct.unl.pt/QOF/TPQO/: site em portugus, ricamente ilustrado, que explica como realizar montagens clssicas
de vidrarias.
9) http://www.qmc.ufsc.br/ : voc vai encontrar aulas prticas de qumica orgnica, que podem ser acompanhadas virtualmente,
dicas de segurana, etc.
Muitas universidades brasileiras mantm sites onde voc pode tirar suas dvidas, acompanhar, virtualmente um
experimento qumico, fazer uma pesquisa.
Reserve algum tempo para navegar e voc poder ter muitas e agradveis surpresas.
Consideraes relevantes:
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Modelo de Capa para o Relatrio de Aulas Prticas

Universidade Vale do Rio Doce UNIVALE

Relatrio no:_______________________________
Disciplina:_________________________________
Assunto:_____________________________________
Grupo responsvel:

Data:______

PRTICA No 1

Determinao do ponto de fuso de

compostos orgnicos
Trabalho pr-laboratrio:
1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2) Defina ponto de fuso.

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3) Defina ponto de decomposio.
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4)

Em que situao uma mistura possui o ponto de fuso definido?

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5) Qual a diferena entre ponto de fuso e faixa de fuso?
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Material: tubo de Thiele, termmetro, tubos capilares, bico de gs, tela de amianto, suporte, garras, mufa.
Introduo:
O ponto de fuso de uma substncia orgnica pura pode ser definido como a temperatura
na qual a fase slida coexiste com a fase lquida. Termodinamicamente falando, ponto de fuso a
temperatura na qual a presso de vapor na fase slida igual presso de vapor na fase lquida.
Nesta situao, as duas fases esto em equilbrio.
A maioria dos compostos orgnicos sofre fuso geralmente em temperaturas
compreendidas entre 50 e 300 oC. Uma substncia orgnica pura geralmente possui um ponto de
fuso bem definido, ou seja, a fuso ocorre em uma faixa estrita de temperatura. Esta propriedade
pode ento ser um critrio de pureza de uma substncia, pois duas amostras de um mesmo composto
devem fundir-se a uma mesma temperatura. Entretanto, duas amostras desconhecidas que se fundem
a uma mesma temperatura no so necessariamente o mesmo composto. Assim, a uria e o cido
cinmico fundem a 133 oC; (-)cido mlico e cido p-metoxibenzico, 100 oC. cido pcianobenzico e 1,5-dinitronaftaleno, 214 oC.
Uma mistura de dois compostos normalmente funde a uma temperatura inferior que
qualquer um dos componentes da mistura. Esta depresso uma caracterstica do ponto de fuso, e
de grande valor quando se quer identificar uma substncia desconhecida.
Na determinao de ponto de fuso, depresses de 05 a 06 oC so raras, mas de cerca de
20 oC so comuns. Duas amostras que se fundem a uma mesma temperatura e cujo ponto de fuso da
mistura no diminui, so consideradas idnticas, com raras excees. Impurezas tambm fazem com
Determinao de ponto de fuso
que o ponto de fuso de qualquer amostra seja menor que aquele da amostra pura, alm de provocar
um alargamento da faixa de fuso.
Embora substncias puras geralmente apresentem pontos de fuso ntidos, muitas fundem-se em intervalos maiores de
temperatura; algumas decompem-se antes da fuso, outros decompem-se no ponto de fuso. Tais pontos de decomposio (a
temperatura na qual o material se decompe) podem ser ntidos o bastante para constituir um valor na identificao. Um composto
que funde com decomposio, normalmente exibe uma faixa de fuso mais larga do que aquela de um composto que no se
decompe.
difcil determinar o ponto de fuso de um composto puro a um grau mais prximo, com a aparelhagem comumente
utilizada em laboratrio de Qumica. Nesta situao, vrias so as fontes de erro termmetros no calibrados (inexatos), diferenas
na velocidade de aquecimento do aparato, diferena nos tipos de aparelhos utilizados, bem como o tipo de vidro usado no recipiente
da amostra, que podem alterar o ponto de fuso observado.
Devido a tais erros, cuidados devem ser observados no uso de tabelas de ponto de fuso para a identificao de
compostos desconhecidos. Se um dos desconhecidos tem ponto de fuso abaixo de 200 oC, todo composto conhecido que funde a 5
o
C daquele valor dever ser considerado. Se o desconhecido funde acima de 200 oC, esta faixa dever ser aumentada para mais ou
menos 10 oC. Inmeros compostos devero ser considerados possivelmente idnticos a uma amostra desconhecida.
Uma das formas de se determinar o ponto de fuso de uma substncia a utilizao de tubos capilares, juntamente com
um tubo de Thiele (Figura 1) como banho de aquecimento. A amostra colocada em um tubo capilar e este preso ao termmetro
por meio de um anel de borracha. A amostra deve estar prxima ao bulbo do termmetro e o anel de borracha acima do nvel do
leo.
Parte experimental
Parte 1: Determinao do ponto de fuso de uma substncia pura.
Tomar uma pequena alquota da amostra pulverizada e coloc-la em um tubo capilar prprio para determinao de ponto
de fuso. Fixar o capilar no bulbo de um termmetro. Mergulhar o conjunto em lquido (leo de cozinha, nujol, silicone) contido no
tubo de Thiele, com cuidado para que a borracha que prende o tubo no toque o lquido. Aquecer o lquido gradualmente,
observando o material no interior do capilar. Devem ser registradas a temperatura em que a primeira gota de lquido se forma e
aquela em que os ltimos cristais desaparecem.
Parte 2: Construo de um diagrama de composio/ponto de fuso .
Preparar 5 misturas diferentes de substncias A e B nas propores molares de 1:9, 3:7, 5:5, 7:3 e 9:1. Introduzir as
misturas finamente pulverizadas em tubos capilares diferentes e determinar os pontos de fuso correspondentes. Determinar o ponto
de fuso de A e B separadamente. Construir a curva de PF das misturas, lanando a composio da mistura na abscissa e a
temperatura de fuso na ordenada. Considerar que a temperatura de fuso seja aquela na qual a mistura se liqefaz completamente.
Observaes relevantes:
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PRTICA No 1

Determinao do ponto de fuso de

compostos orgnicos
Estudante:___________________________________________________________
amostra

1)

PF (literatura)

PF (encontrado)

Utilizando o espao reservado, elabore uma curva- padro para o termmetro que voc est utilizando.

2) Qual(ais) o(s) objetivo(s) desta prtica?

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3)

Quais os cuidados que devem ser tomados na determinao do ponto de fuso de uma substncia orgnica?

4)

Em seu laboratrio, voc precisa determinar o PF de uma amostra. Entretanto, seu termmetro no confivel. O que voc
deve fazer?
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5) Que concluses podem ser tiradas da experincia da Parte 2?

6)

Qual a influncia da quantidade de amostra no ponto de fuso observado?

7)

Por que no aconselhvel a utilizao de gua para o banho de aquecimento?

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PRTICA No 2

Purificao atravs da tcnica de

recristalizao
Trabalho pr-laboratrio:
Amostras utilizadas:

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1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2) Qual(ais) o(s) objetivo(s) desta prtica?

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2) Defina recristalizao.
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3) Quais as caractersticas do solvente ideal para ser utilizado na recristalizao de uma substncia?
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Material: bquer de 125mL, bquer de 250mL, termmetro, basto de vidro, esptula, funil de bchner, kitasato, papel de filtro,
rolhas de borracha, tubos de ensaio, bico de gs, trompa de vcuo, tela de amianto, trip.
Introduo:
A recristalizao o mtodo mais comum de purificao de substncias slidas. A seqncia de eventos para o
procedimento vai depender de quo impura est a substncia e quo solvel esta substncia em vrios tipos de solvente.
importante observar a substncia a ser recristalizada: se cristalina, se existe colorao, etc. Esta observao
importante pois:
1) Cor em uma substncia supostamente branca uma impureza;
2) Cor em uma substncia colorida no uma impureza;
3) Cor errada em uma substncia uma impureza.
Para a recristalizao, trs coisas so muito importantes:
1) Encontrar um solvente no qual a amostra solvel a quente;
2) O mesmo solvente no deve solubilizar a amostra quando estiver frio;
3) O solvente frio deve manter as impurezas em soluo.
A escolha do solvente deve ser realizada atravs de ensaios em tubo: deve ser observada a ao de vrios solventes a frio
e temperatura de ebulio, a formao de cristais durante o resfriamento e o volume de solvente necessrio por grama de amostra a
ser purificada. s vezes uma mistura de dois solventes mais eficaz que um s solvente. O par mais comum gua-etanol. A
tcnica consiste em aquecer o material a ser purificado no solvente no qual mais solvel e adicionar o outro solvente at aparecer
uma turvao.
Durante a solubilizao do material a quente, deve ser usada a menor quantidade de solvente possvel, para diminuir
perdas.
Impurezas coloridas ou resinosas podem ser eliminadas pela adio de carvo ativo. O procedimento consiste em
adicionar uma pequena quantidade soluo a ser aquecida, deixar em ebulio e ento filtrar quente, utilizando o funil de
bchner.
O filtrado deve ser transferido CUIDADOSAMENTE para o frasco de recristalizao, que deve estar perfeitamente
limpo e seco, de forma que no haja "respingos" nas paredes.
Aps a filtrao, o filtrado obtido deve ser mantido em repouso, por 24 horas, para recristalizar. O resfriamento rpido
faz com que haja formao de cristais muito pequenos que adsorvem as impurezas em soluo. Os cristais formados devem ser
separados por filtrao em funil de bchner.
Parte Experimental:
Parte 1: Escolha do solvente:
Pesar cerca de 0,5g de cada uma das amostras a serem testadas. Dividir cada amostra em trs pores iguais. Adicionar
uma poro (A) em um tubo de ensaio contendo 2mL de gua, agitar e anotar a solubilidade. Se a dissoluo no for completa,
aquecer o tubo em bico de gs, observar e anotar o resultado.
Tomar uma outra poro (B) e repetir o procedimento, utilizando etanol como solvente. ATENO: PARA O
AQUECIMENTO, SE NECESSRIO, UTILIZAR BANHO-MARIA (CUIDADO!).
Da mesma forma, tomar uma outra poro (C) e repetir o procedimento utilizando benzeno como solvente. CUIDADO!!
BENZENO EXTREMAMENTE TXICO! EVITAR A INALAO.
Parte 2: Recristalizao de uma amostra comercial
Em dois bqueres limpos e secos, colocar cerca de 1g de cido benzico e adicionar 15mL de H2O., agitando at
dissoluo completa. Aquecer ebulio e a um dos bqueres, adicionar carvo ativo. Manter ebulio por alguns segundos.
Filtrar as solues a quente. Transferir o filtrado para um bquer limpo e deixar em repouso. Filtrar os cristais formados, secar e
pesar.

Observaes relevantes:
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PRTICA NO 2
Purificao atravs da tcnica de
recristalizao
Estudante:__________________________________________________________
Amostras

gua
Fria

Etanol
Quente

Frio

Benzeno
Quente

Frio

Quente

1) Qual a funo do carvo ativo?

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2)

Em que situao utilizado o funil de bchner?

3) Quais os cuidados que devem ser tomados quando realizar a recristalizao?

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4)

Por que a filtrao deve ser feita a quente?

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5)

Por que se recomenda que a soluo seja resfriada espontaneamente, aps ser aquecida?

6) Fornea as caractersticas fisicoqumicas do cido benzico.

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PRTICA No 3

Purificao de substncias atravs da

tcnica de sublimao
Trabalho pr-laboratrio:
1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2)

Qual(ais) o(s) objetivo(s) desta prtica?

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3) Defina sublimao.
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Material: bquer de 100mL, termmetro, esptula, kitasato, rolhas de borracha, tubo de ensaio, bico de gs, trompa de vcuo,
tela de amianto, trip.
Introduo:
A sublimao um processo de purificao de substncias slidas que apresentam presso de vapor relativamente alta
abaixo do seu ponto de fuso. A sublimao ocorre quando um slido aquecido e passa diretamente para o estado de vapor, sem
passar pelo estado lquido.
Poucas so as substncias que possuem presso de vapor suficientemente elevada para permitira sublimao a presso
atmosfrica (por exemplo, naftaleno, antraceno, cafena, cnfora, etc.). Devido a este fato, o mtodo pouco utilizado em
laboratrio, apesar de o sublimado ser obtido geralmente com um alto grau de pureza.
Estas substncias "sublimveis" possuem caractersticas pouco polares e so geralmente razoavelmente simtricas. Nesta
situao, as foras intermoleculares que atuam no estado slido so mais fracas.
Em um processo reverso (esfriamento do vapor) o vapor volta fase slida. Assim, sublimao a passagem de um
slido para a fase de vapor e condensao a passagem de vapor para o estado lquido ou para o estado slido. O termo
"ressublimao" inadequado para este processo.
Parte Experimental:
Parte 1: Sublimao a presso normal.
Em um bquer de 100mL, pesar cerca de 3g da amostra. Cobrir o bquer com um vidro de
relgio, e sobre este, colocar cubos de gelo. Aquecer o bquer lentamente, observando a formao de
cristais. Ao trmino do processo, raspar os cristais e pesar o material purificado.
Determinar o ponto de fuso da substncia pura e comparar com aquele determinado para
a amostra impura.
Sublimao a presso reduzida
Parte 2: Sublimao a presso reduzida.
Em um kitasato de 125mL, colocar cerca de 3g da amostra impura. Conectar um tubo de ensaio contendo gelo ao
kitasato, de forma que o tubo no toque na amostra. Conectar a trompa de vcuo ao sistema e iniciar o vcuo lentamente, para
diminuir perdas. Ao final da sublimao abrir o sistema CUIDADOSAMENTE. Raspar os cristais do tubo, pesar.

Observaes relevantes:
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o

PRTICA N 3

Purificao de substncias atravs da

tcnica de sublimao
Estudante:___________________________________________________________
Amostras:

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1) Quais os cuidados que devem ser tomados quando realizar a sublimao?
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3) Por que a sublimao facilitada se a operao for conduzida a vcuo?
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4)

Qual a funo do gelo?

5)

Fornea exemplos, alm daqueles citados aqui, de substncias sublimveis temperatura ambiente.

6)

Pesquise outras tcnicas que podem ser utilizadas para a purificao de substncias orgnicas, alm daquelas que voc
conhece.

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PRTICA No 4

Anlise qualitativa orgnica

Trabalho pr-laboratrio:
1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2) Qual(ais) o(s) objetivo(s) desta prtica?

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3) Fornea a equao geral de combusto.
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4) Quais os cuidados devemos observar ao trabalhar com sdio metlico?
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Material: Tubos de ensaio, bquer, conexes de vidro, rolhas de cortia, garras de madeira, bico de gs.

Reagentes: Solues aquosas a 10% de: Ba(OH)2, FeSO4, H2SO4, cido actico, acetato de chumbo, HNO3, AgNO3. Soluo de
FeCl3 a 1%, sdio metlico, xido cprico.
Introduo:
Os elementos mais comuns nos compostos orgnicos so o carbono, hidrognio, oxignio, nitrognio, enxofre e
halognios. A evidncia da natureza orgnica de uma determinada amostra pode ser verificada atravs de um ensaio direto que
constata a presena de C e H. Neste mtodo, a substncia orgnica queimada em presena de xido de cobre e o CO2 formado
turva uma soluo de hidrxido de brio, confirmando a presena de carbono, enquanto as gotculas de gua nas paredes do tubo
confirmam a presena de H.
Nitrognio, enxofre e os halognios so caracterizados em compostos orgnicos pela converso em substncias
inorgnicas ionizveis, de forma que se possa aplicar os ensaios inicos das anlises qualitativas. O melhor procedimento consiste
em fundir o composto orgnico com sdio metlico (ensaio de Lassaigne), para que ocorra a formao de cianeto de sdio e haletos
de sdio, que podem assim ser identificados.
NaX
NaCN + NaOH
Na2S

composto orgnico + Na
(C, H, O, N, S, X)

A soluo alcalina resultante da ao da gua sobre o sdio fundido filtrada e tratada com sulfato ferroso, levando
formao, deste modo, de ferrocianeto de sdio. Ao aquecer a soluo alcalina ebulio, so produzidos alguns ons frricos,
devido ao do ar; com a adio de uma soluo diluda de cido sulfrico, os hidrxidos so dissolvidos, formando-se ento o
ferrocianeto frrico (azul da Prssia).
O enxofre, sob a forma do on sulfeto, pode ser identificado pela precipitao do sulfeto de chumbo, que se forma pela
reao com a soluo de acetato de chumbo e cido actico.
A presena de halognios indicada sob a forma de haletos de prata caracterizados pela adio de soluo de nitrato de
prata e cido ntrico diludo.
No existe mtodo direto de caracterizao do oxignio.
Parte Experimental:
Parte 1: carbono e hidrognio:
Misturar bem cerca de 0,1g da amostra com cerca de 2,0g de CuO seco. Colocar a mistura
em um tubo de ensaio seco (I), preso em um suporte, conforme a figura; ligar ao tubo uma rolha
atravessada por um tubo de vidro em um ngulo reto, com a outra extremidade tocando a superfcie
de uma soluo lmpida de Ba(OH)2, contida em outro tubo de ensaio (II). Aquecer a mistura com
uma chama. Um precipitado branco ir se formar no tubo II, devido liberao de CO2. A presena
de hidrognio pode ser notada pela presena de gotculas de gua nas paredes do tubo.
Parte 2: nitrognio, halognio e enxofre:
Em um tubo de ensaio, colocar cerca de 0,2g da amostra e um pequeno pedao de sdio metlico recm-cortado. Prender
o tubo com uma garra e aquecer a mistura fortemente at que o tubo se torne vermelho e haja decomposio completa. Deixar
esfriar. Mergulhar o tubo em um bquer contendo cerca de 20mL de etanol. Quebrar o tubo dentro do bquer. CUIDADO!! O
excesso de sdio ainda pode reagir violentamente se houver gua presente. Os ons e substncias formadas se dissolvem. Filtrar e
usar o filtrado lmpido para os testes de N, S, e halognios.
O excesso de sdio necessrio, pois se S e N estiverem presentes, pode ocorrer a produo de tiocianato de sdio;
assim, no ensaio para nitrognio, poder haver a produo de cor vermelha com o on Fe+3 , ao invs da produo do azul da Prssia,
pois no haver ons CN- livres. Com o excesso de sdio, se houver formao de tiocianato, este se decompor, conforme a equao:

NaCNS + 2Na

NaCN +Na 2S

MANUSEAR SDIO COM CUIDADO!!

Enxofre: Tomar 1-2mL da soluo e acidificar com cido actico; juntar gotas de soluo de acetato de chumbo. A
formao de um precipitado preto confirma a presena de enxofre.

PbS + 2CH3 COONa

3

Na 2S + (CH 3COO) 2Pb

Halognios: Acidificar 1-2mL da soluo com HNO3 e juntar gotas de soluo de AgNO3. A formao de precipitado
branco ou amarelado indica a presena de halognio.

NaX + AgNO

AgX + NaNO

Nitrognio: Tomar 1-2mL da soluo, juntar duas gotas de sulfato ferroso e aquecer por dois minutos. Adicionar uma
soluo de H2SO4 a 10%, gota a gota, para dissolver o Fe(OH)2.

Na4 Fe(CN) 6

NaCN + FeSO4

2 FeSO 4 + H2 SO4 + 1/2 O 2

Na4 Fe(CN) 6 + 2 Fe2(SO4)3

+ 2 Fe2(SO4) 3

Fe 2(SO 4) 3 + H 2O

Na4 Fe(CN) 6

Composto orgnico contendo C, H, N, S, halognio

o

PRTICA N 4

+ 6 Na2SO4

Na2S + NaCNS + NaX

Anlise qualitativa orgnica

Estudante:___________________________________________________________

amostra
Carbono

Hidrognio

ensaios
Nitrognio

Enxofre

Halognios

1) Qual (ais) a (s) concluso (es) a que voc chegou, com relao sua amostra-problema? Discuta.
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PRTICA No 5
Caracterizao de compostos orgnicos
Trabalho pr-laboratrio:
1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2) Qual(ais) o(s) objetivo(s) desta prtica?

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3) Fornea estruturas de alquenos, lcoois primrio, secundrio e tercirio, aldedo, haleto de alquila, cetona e cido carboxlico.
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Material: Tubos de ensaio, bico de gs e conta-gotas.
Reagentes: Solues aquosas a 10%: KMnO4, NaHCO3. Soluo alcolica de AgNO3 a 2%; soluo de cloreto de acetila a 5%;
soluo de bromo em CCl4 a 5%. Reagentes de Fehling e Lucas.
Introduo:
Dentre as funes orgnicas conhecidas, so bastante comuns os alquenos, haletos de alquila, lcoois, aldedos, cetonas e
cidos carboxlicos. Cada uma dessas classes de compostos apresenta reaes especficas, podendo ser utilizadas para sua
caracterizao:
CARACTERIZAO DE ALQUENOS: Consiste na oxidao exaustiva do composto. Os hidrocarbonetos saturados so muito pouco
reativos e portanto, estveis. O teste ser positivo para hidrocarbonetos insaturados. O reagente de Bayer a soluo de
permanganato de potssio em meio neutro. Pode-se usar tambm uma soluo de bromo em tetracloreto de carbono, de cor
avermelhada, com a qual reagem os alquenos, fazendo com que a cor desaparea.
CARACTERIZAO DE LCOOIS: Os lcoois reagem com o cloreto de acetila, produzindo gs clordrico que pode ser detectado.
Os lcoois podem ser primrios, secundrios e tercirios e podem ser diferenciados pelo teste de Lucas. O reagente de Lucas pode
reagir com lcoois numa reao de substituio nucleoflica da hidroxila. Os reagentes e as condies de reao indicam que o
processo envolve a formao de carboctions:

RO H + C l

H
- H 2O

R Cl

A reao rpida para lcoois tercirios, lenta para secundrios e muito lenta para primrios, devido estabilidade do
carboction formado. Como os haletos so insolveis na gua, a reao pode ser comprovada pelo aparecimento de turvao no tubo
de ensaio.
CARACTERIZAO DE HALETOS DE ALQUILA: Um tomo de halognio em um haleto orgnico pode estar ligado a um carbono
aliftico ou a um tomo de carbono de um sistema aromtico. Esta identificao pode ser feita atravs do teste com a soluo de
nitrato de prata alcolico:

RC l

A gN O 3

A gC l ( pr ecipitado br anco)

CARACTERIZAO DE ALDEDOS E CETONAS: Os compostos carbonlicos fornecem reaes especficas, produzindo

precipitados facilmente reconhecveis. Aldedos e cetonas reagem com 2,4-dinitrofenilhidrazina, um reagente para caracterizao do
grupo carbonila. Se este grupo estiver conjugado a uma ligao dupla, o produto obtido ter colorao avermelhada; se a carbonila
no for conjugada a uma ligao dupla, o precipitado formado ter colorao amarela.
HN

NH2
NO2

R
C

NO2

H2O

O2N

NO2

Os aldedos reagem com o reagente de Fehling, produzindo um precipitado de cobre metlico que se fixa nas paredes,
produzindo um espelho de cobre. Este reagente constitudo de duas solues (sol. I, tartarato duplo de sdio e potssio; sol. II,
sulfato cprico), as quais so misturadas no momento do teste.
-

COO Na

Na OOC
H
alde do

Cu
H

OH

OH

+
H

Cu

OH

K OOC

C u 2 O ou

COO K

CARACTERIZAO DE CIDOS CARBOXLICOS: Estes compostos so substncias cidas que podem reagir com lcalis. Com
uma soluo de bicarbonato de sdio, os cidos carboxlicos reagem, com a formao de CO2 que pode ser facilmente visualizado.
Parte Experimental:
Parte 1: Teste para alquenos:
Em um tubo de ensaio contendo 1mL de soluo de KMnO4, adicionar a amostra. O descoramento da soluo violeta e
formao de um precipitado marrom indicam que o hidrocarboneto insaturado.
confirmao: TESTE DE BROMO: Adicionar cerca de 4 gotas da amostra em um tubo de ensaio limpo. Adicionar
CUIDADOSAMENTE, 10 gotas de uma soluo de bromo em CCl4. O desaparecimento da cor confirma a presena de ligao
mltipla carbono-carbono.
Parte 2: Teste para lcoois:
Em um tubo de ensaio contendo a amostra, adicionar gota a gota e sob agitao, cloreto de acetila. Aquecer a mistura em
bico de gs. Se o desconhecido for um lcool, a reao ocorre com desprendimento de HCl, que pode ser evidenciado com um
pedao de papel indicador umedecido com gua, que ser colocado na boca do tubo. O papel de tornassol azul torna-se roas.
Diferenciao entre lcoois primrios, secundrios e tercirios: TESTE DE LUCAS: Em um tubo de ensaio contendo 2mL do
reagente de Lucas (13,6g de cloreto de zinco em 89mL de cido clordrico concentrado), adicionar 0,5mL do lcool. Fechar o tubo e
anotar o tempo de aparecimento de uma turvao ou a formao de uma segunda camada de lquido.
Parte 3: Teste para haletos de alquila:
Em um tubo contendo cerca de 1mL de uma soluo a 2% de nitrato de prata em lcool etlico, adicionar gotas da
amostra. Agitar e anotar o tempo necessrio para a formao de um precipitado; isto indicar a presena de um haleto allico. Os
haletos de arila no formam precipitados.
Parte 4: Teste para compostos carbonlicos:
Em um tubo de ensaio, colocar cerca de 0,5mL (ou 0, mg) da amostra e adicionar 1mL de etanol e 2mL do reagente 2,4dinitrofenilhidrazina (3g de 2,4-dinitrofenilhidrazina dissolvidos em 15mL de H2SO4. Adicionar 20mL de H2O e 70mL de etanol.
Agitar bem e filtrar). Agitar e deixar em repouso por 15 minutos. Observar.
Teste para diferenciar aldedos de cetonas: Em um tubo de ensaio, colocar 1mL da soluo I, adicionar 1mLda soluo II e agitar.
Adicionar a amostra e aquecer em um bico de gs. O aparecimento de um precipitado vermelho tijolo (ou o espelho de cobre) indica
a presena de aldedo.
Parte 5: Teste para cidos carboxlicos:
Adicionar amostra, cerca de 1mL de soluo 0,5M de NaHCO3. A evoluo de CO2 indica a presena de grupo
carboxila, uma vez que cetonas, aldedos ou lcoois no reagem nessas condies.

PRTICA No 5

Caracterizao de compostos orgnicos

Estudante:___________________________________________________________
Ensaios
Amostra

Alqueno
Primrio

lcool
Secundrio

Haleto

Aldedo

Cetona

cido

Tercirio

1)

Discuta os resultados obtidos.

2)

Qual (ais) a (s) concluso (es) a que voc chegou, com relao sua amostra-problema? Discuta.

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o

PRTICA N 6

Identificao de lcoois e fenis.

Trabalho pr-laboratrio:

1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2)

Qual(ais) o(s) objetivo(s) desta prtica?

3)

Fornea exemplos de estruturas de um lcool primrio, um lcool secundrio e um lcool tercirio.

4)

Por que, em geral, os lcoois so mais solveis em gua que hidrocarbonetos?

5)
Qual a principal caracterstica qumica do fenol?
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Material: papel indicador, tubos de ensaios, conta-gotas, banho-maria, pinas de madeira

Reagentes: fenol, acetona, cido crmico, soluo de cloreto frrico, soluo de I2-KI, butanol, isobutanol, lcool t-butlico, fenol
Introduo:
lcoois so substncias comercialmente importantes, pois so utilizados como solventes, medicamentos, desinfetantes e
como material de partida para a sntese de diversas outras substncias. Fenis so relacionados aos lcoois devido presena, em
sua estrutura, do grupo hidroxila. Entretanto, como o grupo hidroxila est ligado diretamente a um anel aromtico, as propriedades
qumicas dos fenis so diversas daquelas dos lcoois.
lcoois e fenis so polares, devido presena da hidroxila, que possibilita a formao de ligaes de hidrognio. Fenis
so mais cidos que os lcoois e suas solues concentradas so muito txicas.
O comportamento qumico das diferentes classes de lcoois e fenis pode ser utilizado como uma forma de identific-los.
1) Teste de Lucas: J realizado anteriormente (ver Prtica no 5), utilizado para distinguir entre lcoois primrios, secundrios e
tercirios. Pela adio deste reagente, um lcool tercirio reage rapidamente, um lcool secundrio reage lentamente e, aps um leve
aquecimento, fornece uma frao imiscvel com gua , passados cerca de 10 min. Um lcool primrio no reage nas condies do
teste.
no reage
CH3CH2OH + HCl + ZnCl2
lcool primrio
(CH3)2CHCl + H2O (10 min. aps aquecimento)

(CH3)2CHOH + HCl + ZnCl2

lcool secundrio
(CH3)COH

+ HCl + ZnCl2

(CH3)2CCl + H2O

(5 min. )

lcool tercirio

2) Teste do cido crmico: Possibilita a diferenciao de lcoois primrios e secundrios dos lcoois tercirios. Em contato com
uma soluo acidificada de dicromato, lcoois primrios so oxidados a aldedos; lcoois secundrios so oxidados a cetonas;
lcoois tercirios no reagem. Durante a oxidao, a cor marrom-avermelhada do cido crnico muda para uma soluo azulesverdeada. Fenis so oxidados, fornecendo uma massa marrom.
O
3 CH3CH2OH + 4 H2CrO4 + 6 H2SO4
lcool primrio

3 CH3COH + 2 Cr2(SO4)3 + 13 H2O

O

marrom-avermelhado

azul-esverdeado

3 CH3CCH3 +

(CH3)2CHOH + 2 H2CrO4 + 3 H2SO4

lcool secundrio marrom-avermelhado
(CH3)COH
lcool tercirio

H2CrO4 +

Cr2(SO4)3 + 8 H2O
azul-esverdeado

no reage

H2SO4

3) Teste do iodofrmio: Este teste mais especfico que os dois anteriores. Somente o etanol e lcoois que possuam em sua estrutura
uma parte CH3CH(OH)R reagem. Estes lcoois reagem com iodo em soluo aquosa de NaOH fornecendo o precipitado amarelo
de iodofrmio.
O
OH
RCHCH3

+ 4 I2 +

RC

6 NaOH

O Na

+ 5 NaI + 5 H2O + HCI3

iodofrmio

Fenis tambm reagem sob estas condies. Com o fenol, forma-se o precipitado amarelo do triiodofenol.
OH

OH
I

+ 3 I2

1-

Acidez dos fenis: O fenol tambm chamado de cido carblico. Reage com base, facilmente se dissolvendo em um soluo
bsica. Em contraste, nas mesmas condies, os lcoois no so to cidos.
-

OH

+ OH-

2-

2,4,6-triiodofenol

+ H2O

Teste do cloreto frrico: A adio de soluo aquosa de cloreto frrico a um fenol fornece uma soluo colorida que,
dependendo da estrutura do fenol, pode variar de verde a prpura.
OH

Fe

Cl

Cl

Parte Experimental:

+ FeCl3
amarelo claro

+ HCl
violeta

Parte 1: Teste de solubilidade:

Em tubos de ensaio separados, adicionar 10 gotas de 1-butanol, 2-butanol, 2-metil-2-propanol, da soluo aquosa de
fenol e da amostra desconhecida. Adicionar 2 mL de gua. Observar. Todas as solues so homogneas?
Parte 2: Teste de acidez:
Utilizando as mesmas solues da parte 1, testar o pH de cada soluo.
Parte 3: Teste do cido crmico:
Em tubos de ensaio secos e identificados, colocar 5 gotas da amostra desconhecida, bem como os lcoois citados na Parte
1. Adicionar 5 gotas de uma soluo de dicromato de potssio a 5% e 5 gotas de cido sulfrico a 10%. Aquecer os tubos em banhomaria (cerca de 60 oC) (CUIDADO!) por 5 minutos. Observar a cor de cada soluo.
Parte 4: Teste do iodofrmio:
Em tubos de ensaio secos e identificados, colocar 5 gotas da amostra desconhecida e dos lcoois citados. Adicione a cada
tubo, lentamente, 15 gotas de uma soluo de NaOH 6M. Agite o tubo. Aquecer a mistura em banho-maria (cerca de 60 oC).
Adicionar, gota a gota e com agitao, a soluo de I2-KI, at a soluo tornar-se marrom (aproximadamente 25 gotas). Adicione a
cada tubo, lentamente, gotas da soluo de NaOH 6M, at a soluo tornar-se incolor. Manter os tubos no banho-maria por 5
minutos. Remover os tubos do aquecimento, esfriar e observar se houve a formao de um precipitado amarelo claro.
Parte 5: Teste do cloreto frrico:
Em tubos de ensaio secos e identificados, colocar 5 gotas da amostra desconhecida e dos lcoois citados. Adicionar 2
gotas de soluo de cloreto frrico. Observar qualquer alterao de cor.
Observaes relevantes:
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PRTICA No 6
Identificao de lcoois e fenis
Estudante:___________________________________________________________
Testes

Amostras

Solubilidade
Acidez
cido crmico
Iodofrmio
Cloreto frrico

1) Fornea as estruturas dos lcoois utilizados nos testes.

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2)

Fenis e lcoois fornecem produtos diferentes quando submetidos reao com I2-KI. As reaes que ocorrem so
semelhantes? Se no, justifique.
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3)

Por que, diferente dos lcoois primrios e secundrios, os lcoois tercirios no reagem com cido crmico?

4) Fornea exemplos, diferentes daqueles que voc viu neste experimento, de lcoois utilizados na indstria.
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o

PRTICA N 7

Identificao de carboidratos
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

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2) Definir carboidratos .
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3) Definir monossacardeos, dissacardeos, oligossacardeos e polissacardeos, fornecendo exemplos.
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Material: Tubos de ensaio, conta gotas, bico de gs, provetas de 10mL, banho-maria, pinas de madeira.
Reagentes: Soluo de iodo, reagente de Fehling, reagente de Tollens, soluo de HCl 3M. Soluo de NaOH 3M, Soluo de
NaOH 20%, papel indicador, reagente de Seliwanoff, reagente de Bial, soluo de cloreto de metilamnio.
Introduo:
Carboidratos so aldedos ou cetonas poliidroxilados ou compostos que, por hidrlise, do origem a aldedos e/ou cetonas
poli-hidroxiladas. Arroz, batata, frutas etc., so fontes ricas em carboidratos. Estas substncias podem ser classificadas como
monossacardeos (p.ex., glicose, frutose), dissacardeo (sacarose, lactose) ou polissacardeos (amido, celulose), que podem consistir
de vrias, s vezes centenas, de monossacardeos ligados uns aos outros. Geralmente monossacardeos existem na forma cclica,
contendo grupos hemiacetal ou hemicetal. Estas estruturas, quando em soluo, permanecem em equilbrio com as respectivas
formas abertas.
hemiacetal
CH2OH
H
H
O
H
OH H
OH
HO
H

OH

-D-glicose

CH2OH
H

O
H
C
OH H

HO
H

H
H
O

OH

forma de cadeia aberta

CH2OH

hemiacetal

O OH
H
OH H
H
HO
H

OH

-D-glicose

Dissacardeos e polissacardeos existem como estruturas cclicas contendo grupos funcionais como hidroxila, acetal (ou
cetal), carboxila, hemicetal (ou hemiacetal).

Quando a unidade osdica final contm um grupo hemiacetal (ou hemicetal) na sua frao terminal chamada de acar
redutor. Quando no possui um hemiacetal (ou hemicetal) na frao terminal, chamada de acar no-redutor. O nome "redutor"
dado pelo fato de que hemiacetais (e em menor extenso hemicetais) poderem reduzir alguns agentes oxidantes.
CH2OH
CH2OH
O H H
O H
H
1 4 H
Maltose
OH H
OH H
O
OH
HO

CH2OH
H
O H CH2OHO
H
Sacarose
OH H
OH
H
O
CH2OH
HO
H OH
OH H

OH

final no-redutor

OH

final redutor

Quando um acar no-redutor (p. ex. sacarose, amido), hidrolisado, a ligao glicosdica (acetal) rompida e uma
frao terminal redutora formada. Esta hidrlise pode ser obtida em meio cido ou por meio de ao enzimtica.
O amido, quando em contato com iodo, d origem a um complexo de cor azul escura ou violeta, intensa e brilhante,
devido formao de cadeias helicoidais que capturam a molcula de iodo. Este complexo lbil e pode ser decomposto pelo
aquecimento. Quando o amido hidrolisado e quebrado em pequenas cadeias osdicas, no possvel a formao deste complexo e
a cor azul no observada.
Parte Experimental:
Parte 1: Teste do iodo (soluo estoque: 2g de KI em 50mL de gua; adicionar 1g de iodo e agitar at dissoluo):
Adicionar algumas gotas da soluo de iodo a cerca de 2mL da amostra. O aparecimento de cor azul intensa indica a
presena de amido.
Parte 2: Teste de Fehling:
Misturar 1mL da soluo A com 1mL da soluo B em um tubo de ensaio e adicione 2mL da amostra. Aquecer a mistura
at a ebulio (CUIDADO!!). O aparecimento de precipitado vermelho tijolo indica a presena de acares.
Parte 3: Teste de Tollens:
Em um tubo de ensaio, adicionar 2 gotas de uma soluo de NaOH a 5% a 2mL de uma soluo de AgNO3 a 5%.
Adicionar gotas de soluo de NH4OH at que o precipitado formado se dissolva. Adicionar 2mL da amostra e aquecer em banhomaria (aprox. 60 oC), por cerca de 10min. H formao de espelho de prata, em presena de acar.
Parte 4: Hidrlise de polissacardeos:
Misturar 1mL de HCl (3M) com 5mL da amostra. aquecer em banho-maria por 10min. Neutralizar a soluo com NaOH
diludo. Utilizar o hidrolisado para fazer o teste de Fehling.
Parte 5: Teste de Seliwanoff (teste para cetoexoses): (Soluo estoque: 0,5g de resorcinol em 1000mL de HCl 3M).
Em trs tubos de ensaio separados, cada um contendo 2mL de reagente de Selliwanof, adicionar 2 gotas de soluo de
frutose, 2 gotas de soluo de glicose e 2 gotas da amostra. Aquecer cada tubo em banho-maria, por cerca de 8min. Comparar o tubo
contendo a amostra, com aquele contendo frutose (padro).
Esquema de trabalho:
A/B/C/D

(+) amido

I2
(-)

frutose/ glicose/ sacarose

Fehling ou Tollens

(-) sacarose

(+)

Confirmar com hidrlise cida, seguida

por ensaio de Fehling ou Tollens

frutose/ glicose
Seliwanoff

(- ) glicose

(+) frutose

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o

PRTICA N 7

Identificao de carboidratos

Estudante:___________________________________________________________
Amostra

Testes
Iodo

Fehling

Tollens

Seliwanoff

1) Qual teste qumico pode ser utilizado para indicar se houve a hidrlise completa do amido?
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2)

Fornecer a estrutura da amilose. Esta substncia fornece um teste de iodo positivo e um teste de Fehling negativo. Baseando
em sua estrutura, explicar estes resultados.
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3)

Esquematize as estruturas da glicose, frutose e sacarose.

4)

Fornea exemplos, diferentes daqueles que voc viu neste experimento, de carboidratos utilizados na indstria e suas
aplicaes.
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PRTICA No 8
Cromatografia em Camada Delgada
Trabalho pr-laboratrio:

1) Qual (ais) o(s) objetivo(s) desta prtica?

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2)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

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3) Defina Rf.
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4) Que fatores dificultam a reprodutibilidade dos valores de Rf na CCD?

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Material: tubo capilar, placas cromatogrficas, cubas de vidro
Introduo:
Cromatografia um processo de anlise que pode ser utilizado para purificar, separar, identificar ou dosar substncias
orgnicas e inorgnicas, tendo como base a diferena de velocidade com que as substncias se movem atravs de um meio poroso
(fase estacionria), quando arrastadas por um solvente (fase mvel ou eluente) em movimento. Este movimento depende da
interao existente entre a amostra e a fase mvel e a fase estacionria (coeficiente de distribuio).
A cromatografia pode ser normal ou em fase reversa, sendo esta utilizada para substncias muito polares (p. ex.,
acares, protenas, etc.); plana ou em coluna; lquida ou gasosa.
1) Cromatografia por partio: Tipo de cromatografia na qual os componentes da amostra so eludos, de acordo com a sua
afinidade com o solvente utilizado como eluente, ou seja, baseia-se na diferena entre a solubilidade relativa dos componentes da
amostra em solventes imiscveis. Assim, na cromatografia normal, quanto menos polar a substncia, mais rapidamente ser arrastada
(eluda) pelo solvente.
Ex.: Cromatografia em papel: Uma soluo da amostra aplicada prxima extremidade de uma folha de papel de filtro
quadrangular e esta folha colocada em contato com o solvente que se encontra em um recipiente fechado (cmara cromatogrfica),
de maneira a facilitar a ascenso do solvente por capilaridade. O solvente passa sobre a mancha, arrastando os componentes com
velocidades diferentes.

2) Cromatografia por adsoro: Os componentes da amostra so eludos de acordo com o grau de adsoro destes, sobre a
superfcie da fase estacionria, em um determinado sistema de solventes. Neste mtodo, uma substncia diferente do papel
utilizada (slica gel, poliamida, celulose em p, alumina).
Ex: Cromatografia em camada delgada de slica gel. Uma placa de vidro ou folha rgida de plstico ou alumnio revestida com
uma fina camada deste material adsorvente, formando as placas cromatogrficas ou cromatoplacas . O desenvolvimento do
cromatograma deve ser feito em atmosfera saturada com os solventes empregados.
Cromatografia em coluna: Uma coluna de vidro preenchida pelo material adsorvente e a amostra aplicada no topo desta. A
eluio feita utilizando solventes de polaridade crescente e as fraes contendo as substncias isoladas da amostra, so recolhidas
em erlenmeyer.
Na cromatografia plana (em papel ou camada delgada), s vezes desejvel, para fins analticos, o clculo do fator de
reteno (Rf) da amostra. Para uma mesma condio de anlise (mesmo eluente, cmara cromatogrfica, fase estacionria), o Rf de
uma dada substncia ser o mesmo.
Assim, o fator de reteno pode ser calculado:

Rf =

distncia percorrida pela amostra d1

distncia percorrida pelo solvente d2

Os valores de Rf devem ser menores que 1 (um). Quando RFA =0, conclui-se
que a substncia no se deslocou do ponto de aplicao. Se RFA= 1, a
substncia se move junto com o solvente. Em ambos os casos, deve-se escolher
outro eluente.

d2
d1

Parte Experimental:
Parte 1: Preparo das cromatoplacas:
O suporte utilizado ser placas de vidro (ou lminas de microscpio), lavadas com gua e sabo, secas e limpas com um
algodo embebido de acetona, para retirar qualquer vestgio de sujeira ou gordura.. Uma suspenso de slica gel 60G Merck feita
em gua. Esta suspenso distribuda sobre a superfcie das placas de vidro. Manter as placas cromatogrficas em estufa a 105 oC,
com o objetivo de eliminar a umidade (ativao).
Parte 2: Preparo da cmara cromatogrfica (cubas):
Preparar o eluente, de acordo com a amostra a ser analisada. Colocar quantidade suficiente de eluente preparado para que
forme uma camada de cerca de 1 cm na cuba. Tampar a cuba e deixar em repouso para a saturao.
Parte 3: Aplicao da amostra:
A amostra aplicada, com o auxlio de um tubo capilar, a cerca de 0,5cm da base da cromatoplaca. Esta introduzida
verticalmente na cuba, que imediatamente fechada. Deixar que a eluio atinja at cerca de 0,5cm antes do topo da placa. Retirar o
cromatograma, deixar secar. Revelar com reveladores apropriados.
Parte 4: Exemplos de reveladores:
vapor de iodo (revelador universal): a cromatoplaca introduzida em uma cmara contendo iodo metlico. Os vapores de iodo
conferem s manchas uma colorao marrom.
soluo etanlica de H2SO4 20% (revelador universal): a soluo pulverizada sobre a placa e esta aquecida a 105oC por 10min.
H o desenvolvimento de tons de cinza sobre as manchas.
revelador verde de bromocresol (cidos carboxlicos): A placa pulverizada com a soluo alcalina de verde de bromocresol 1%.
Quando em presena de cido carboxlico, h o desenvolvimento

PRTICA No 8
Cromatografia em Camada Delgada
Estudante:__________________________________________________________
Amostras:
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1) Explique o que e para que se faz necessria a ativao das placas cromatogrficas.
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2) Calcule o Rf das manchas no cromatograma.
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3) Qual a funo do gesso?
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o

PRTICA N 9

Separao de pigmentos de plantas:

cromatografia em coluna e em papel
Trabalho pr-laboratrio:

1) Qual(ais) (so) o(s) objetivo(s) desta prtica?

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2) Faa uma reviso dos conceitos bsicos de cromatografia.
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3) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
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Material: Coluna cromatogrfica, tubos de ensaio, 2 bqueres de 150mL, erlenmeyer de

150mL, esptula, basto de vidro, funil, papel de filtro, suporte para funil, garras,
mufas, suportes, pipeta, pera, cmara cromatogrfica, tesoura, tubos capilares,
banho-maria, proveta, balana, ter de petrleo, , l de vidro.
Reagentes: massa de tomate, slica gel 60, -caroteno padro, ter de petrleo, tolueno, etanol,
acetona, gua de bromo saturada, cristais de iodo.
Introduo:
Cromatografia em coluna difere da CCD, pelo fato de que o adsorvente, ao invs de
estar disposto em camada, est contido, como o nome indica, no interior de uma coluna. uma
tcnica rpida que permite separar e isolar, grande quantidade de determinada substncia.
Os adsorventes mais utilizados so a slica gel e a alumina, que colocada em um
tubo de vidro, conforme a Figura. A mistura dissolvida em um solvente adequado e aplicada
no topo da coluna e, ento eluda com o mesmo ou outro eluente (fase mvel).
Cromatografia em papel, o papel adsorve gua da atmosfera e esta gua a fase
estacionria. O(s) componente(s) do sistema de eluio constitui (em) a fase mvel, ou seja, a
cromatografia em papel um sistema lquido-lquido.
A cromatografia em coluna utilizada com propsito preparativo, quando desejvel obter as substncias isoladas na
ordem de mg ou g. A cromatografia em papel, por sua vez, utilizada principalmente com objetivos analticos. Estas duas tcnicas
podem ser utilizadas para caracterizar e isolar pigmentos de origem vegetal.
O tomate, bem como outros vegetais, possui em sua composio qumica pigmentos que conferem ao fruto sua cor
caracterstica. Destes, os principais so o -caroteno (alaranjado) e o licopeno (vermelho).
H3C
CH3

CH3

CH3

CH3

H3C

CH3

CH3

CH3

licopeno

CH3

H3C
CH3

CH3

CH3

CH3

CH3
CH3

H3C

CH3

CH3

-caroteno

As cores destes pigmentos so devidas s numerosas ligaes duplas carbono-carbono em suas estruturas.
Parte Experimental:
Parte 1: Extrao de pigmentos:
Pesar, em um bquer, cerca de 50g de massa de tomate. Adicionar 30mL de etanol e agitar vigorosamente, at a massa de
tomate no mais aderir ao basto de vidro. Colocar uma pequena quantidade de l de vidro no funil (CUIDADO!) e filtrar a mistura.
No final da filtrao, pressionar levemente a l de vidro, para extrair o mximo de lquido do resduo.
Colocar o resduo em um bquer e adicionar cerca de 20mL de ter de petrleo. Agitar a mistura por cerca de 3 minutos, para
extrair os pigmentos. Filtrar o extrato em l de vidro. Concentrar o filtrado em banho-maria (CUIDADO!), at pequeno volume.
Parte 2: Cromatografia em papel:
Cortar um retngulo de papel, com cuidado, de forma a no contamin-lo. Com lpis, traar uma linha no lado mais estreito
do retngulo, a cerca de 1 cm da borda. Aplicar o extrato obtido ao lado de uma soluo padro de -caroteno. Secar bem. Eluir o
cromatograma em mistura ter de petrleo:tolueno:acetona (45:1:5). Aps a eluio, secar o cromatograma e medir o Rf das
manchas obtidas. Se as manchas no ficarem muito visveis, revelar o cromatograma com vapores de iodo.
Parte 3: Cromatografia em coluna:
Tomar uma bureta de 25mL, adicionar um pequeno pedao de l de vidro no fundo da bureta. Adicionar a slica gel
suspendida em ter de petrleo. Quando toda a slica houver sido transferida para a coluna, colocar um pequeno pedao de l de
vidro no topo.
Adicionar, com a ajuda de uma pipeta, o extrato obtido (empacotamento da amostra). Eluir com ter de petrleo, recolhendo
fraes de cerca de 15mL.
Parte 4: Arco-ris de tomate:
Em um bquer, pesar cerca de 15g de extrato de tomate. Adicione cerca de 30mL de gua e agite vigorosamente. Transferir o
suco de tomate obtido para uma proveta de 50mL e, com a ajuda de uma pipeta, adicionar, gota a gota, gua de bromo. Com um
basto de vidro, agitar levemente a soluo. Observar e anotar as cores formadas.

__________________________________________________________________
o

PRTICA N 9

Separao de pigmentos de plantas:

cromatografia em coluna e em papel
Estudante:__________________________________________________________
Amostra:
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1) Defina cromatografia em coluna e cromatografia em papel.

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2) O que a "fase estacionria" de uma coluna cromatogrfica?
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3) E a "fase mvel"?
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4) Qual a diferena entre a slica gel utilizada na CCD e a utilizada na cromatografia em coluna?
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5) Explique as cores formadas no experimento 4.
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6) No que consiste o ter de petrleo?
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7) Qual o objetivo, na parte 1, da extrao com etanol?

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8) Cite outras fontes de -caroteno.
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9)

Para que so utilizados o licopeno e o -caroteno?

10) Qual a diferena bsica entre as estruturas dos dois pigmentos?

11) Os nomes destes pigmentos revelam alguma coisa sobre sua classificao qumica?
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12) Qual a reao que ocorreu no experimento 4?

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PRTICA No 10
Destilao por arraste de vapor
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

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2)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

3)

Faa uma pesquisa sobre a utilizao da destilao por arraste de vapor na indstria.

Material: Suportes, garras, anis, bales de destilao, bales de fundo redondo, condensadores, tubos de vidro, tubos de ltex,
rolhas, bqueres, provetas, funil de separao, prolas de vidro.
Reagentes: ter etlico, plantas aromticas, anilina, sulfato de sdio anidro.
Introduo:
A destilao por arraste de vapor um mtodo de isolamento e purificao de substncias usado desde os tempos
ancestrais. usada para lquidos que so pouco miscveis ou totalmente imiscveis com a gua. O vapor de uma mistura imiscvel a
uma determinada temperatura constitudo dos produtos da mistura e a presso total deste vapor a soma das presses parciais,
segundo a lei de Dalton. Quando a presso P se iguala presso externa, a mistura entra em ebulio e o vapor condensado ser a
mistura dos produtos de presso .
Assim, a mistura entra em ebulio a temperatura inferior temperatura de ebulio de qualquer um dos constituintes da
mistura. Geralmente utiliza-se gua para gerar vapor, que arrasta outros produtos imiscveis, como por exemplo, anilina ou outras
substncias que se decompem facilmente quando aquecidas a temperaturas mais elevadas. tambm utilizada para extrair leos
essenciais que se encontram em clulas vegetais. O vapor aquecido rompe as clulas e arrasta consigo o leo essencial, geralmente
utilizado em perfumes e cosmticos.
H duas formas de gerar vapor: externa e internamente. No primeiro caso, o vapor gerado em um frasco e levado, por
uma tubulao, por exemplo, at o material a ser destilado. a forma clssica de destilao por arraste de vapor.
Na outra forma, interna, o vapor gerado no mesmo frasco onde est inserido o material a ser destilado.
Parte Experimental:
Em um balo de fundo redondo, adicionar o volume de gua correspondente metade de sua capacidade (balo gerador).
Em um outro balo, adicionar 10mL de gua e a amostra. Aquecer o balo gerador at a gua entrar em ebulio e ento conect-lo
ao balo contendo a amostra. Deixar passar o vapor atravs da amostra at que o destilado, que sai do condensador, perca sua
aparncia leitosa ou colorida. Recolher ainda um volume adicional de 10mL.
Retirar o aquecimento e desconectar os dois bales. Transferir o destilado recolhido para um funil de separao e separar,
se possvel, a camada no aquosa. Lavar a camada aquosa com 10mL de ter etlico e juntar a camada orgnica quela recolhida
anteriormente. Medir o volume total obtido. Deixar evaporar o ter e medir o volume novamente.
Os leos essenciais podem ser separados da camada aquosa atravs de um funil de separao. O leo, mais leve,
deixado no funil e lavado com pequeno volume de ter e secado com sulfato de sdio anidro. Pela evaporao do ter obtido o
leo essencial.
Observaes relevantes:
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____

PRTICA No 10
Destilao por arraste de vapor

Estudante:___________________________________________________________
Amostras:
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1) Por que so adicionadas prolas de vidro ?

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2) Todos os tubos de vidro e conexes nesta montagem devem ser os mais curtos possveis. Justifique.
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3)

Para que utilizado o sulfato de sdio anidro?

4) Faa o desenho esquemtico de uma destilao por arraste de vapor.

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PRTICA No 11
Isolamento da cafena
Trabalho pr-laboratrio

1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2)

Qual(ais) o(s) objetivo(s) desta prtica?

3)

Cite algumas fontes de cafena.

4)

De que maneira a cafena afeta um indivduo?

____________________________________________________________________________________
___
Material: Bquer de 250mL; 3 erlenmeyers de 125mL; funil simples; basto de vidro; esptula; funil de separao, papel de filtro,
suporte universal; mufa; anel de ferro; garras; trip; tela de amianto.
Reagentes: Soluo de cido clordrico 1M; sulfato de sdio anidro; hidrxido de amnio; papel indicador; diclorometano
Introduo:
Os conceitos de cidos e bases so extremamente importantes em Qumica Orgnica. A primeira definio surgiu em
1887, proposta pelo qumico sueco Svante Arrhenius. Segundo ele, cidos seriam substncias cujas solues aquosas contivessem
excesso de ons H+ (em relao a OH-), enquanto bases seriam substncias cujas solues aquosas contivessem excesso de ons OH(em relao a H+). Como este conceito limita-se a solues aquosas, surgiram novas definies.
cidos e Bases de Brnsted-Lowry: De acordo com este conceito, cidos so substncias capazes de doar um ou mais prtons (H+)
em uma reao qumica; e bases, substncias capazes de aceitar um ou mais prtons.
B:
base

H-A
cido

B H
cido
conjugado

base
conjugada

A base, ao receber um prton, convertida no cido conjugado; o cido, ao ceder um prton, convertido na base
conjugada.

OH
CH3COOH

Exemplos de compostos orgnicos que apresentam carter cido:

cidos carboxlicos

fenis

Algumas bases comumente utilizadas em Qumica Orgnica:

CH3CH2OK

CH3Li

NH3
NaNH2

NaOH

CH3NH2 e aminas em geral

CH3Na

tente nomear estas bases

Um aspecto importante do conceito de cido e base de Brnsted-Lowry a fora relativa do cido e da base conjugada.
A amnia (NH3), por exemplo, um cido muito mais fraco que a gua, portanto sua base conjugada, o on amideto (-NH2) muito
mais forte que a da gua (-OH).
cidos e bases de Lewis: Proposto pelo qumico americano Gilbert N. Lewis, este conceito bem mais abrangente. Uma base de
Lewis uma espcie que possui pelo menos um par de eltrons no ligantes disponvel para compartilhar com outra espcie, durante
uma reao qumica. Um cido de Lewis uma espcie capaz de aceitar um par de eltrons.
EXEMPLOS:

BASE DE LEWIS

CIDO DE LEWIS
+

OH

H2O

H2O

H3O

BF3

+
-

NH3

F3B NH3

As aminas e outros compostos orgnicos nitrogenados so bases orgnicas, geralmente pouco solveis em gua fria e
solveis em solventes orgnicos pouco polares. Podemos utilizar as propriedades de base para extra-las das plantas que as contm,
bem como para purific-las.
Podemos usar como exemplo, a nicotina, uma amina cclica, pouco solvel em gua: A nicotina recebe um prton,
dando seu cido conjugado, solvel em gua. Em uma reao inversa, em presena de uma base, a nicotina protonada perde um
prton, fornecendo a nicotina, insolvel em gua.

N
N

CH3

CH3

nicotina

OH

N
H
N

CH3

CH3

nicotina

As metilxantinas so compostos orgnicos nitrogenados, dos quais os exemplos mais conhecidos so a cafena (extrada
do caf, ch , guaran, etc.) e a teobromina (extrada do cacau.). Da mesma forma que a nicotina e outras aminas, estes compostos
so bases orgnicas e podemos utilizar as propriedades de base para podermos extra-las das plantas que as contm, bem como para
purific-la.
O
H3C

CH3

N
Parte Experimental:
N
Pesar 20g de cascas de caf modas, em um bquer de 250mL. Adicionar cerca de 30mL
N
O
N
de soluo de HCl 1M e aquecer fervura. Filtrar. Esfriar o filtrado. Transferir a soluo contendo
o sal de cafena para o funil de separao e adicionar NH4OH, at cerca de pH9. Nesta fase, o sal
CH3
formado na soluo cida volta condio de base, insolvel em gua.
cafena
Adicionar cerca de 15mL de diclorometano e agitar. Separar a fase inferior
(orgnica) em um erlenmeyer. Repetir a operao por 3 vezes. No final, desprezar a fase
aquosa alcalina.
Transferir a fase orgnica para o funil de separao e adicionar gua. Desprezar a fase aquosa. Repetir a operao .
Transferir a fase orgnica para um erlenmeyer seco e adicionar o sulfato de sdio anidro. Filtrar em papel de filtro seco.
Aquecer a fase orgnica at secura. Pesar.

PRTICA No 11
Isolamento da cafena
Estudante:___________________________________________________________
Amostra:
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1) Que outros compostos foram extrados com a cafena ?

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2) De que forma estes compostos foram separados da cafena?
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3) Como voc pode saber, sem a ajuda da literatura, que o CH2Cl2 possui densidade maior que a gua?
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4) Para que serve o sulfato de sdio anidro?
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4) Como voc pode testar a pureza de uma amostra de cafena?

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5) Que tcnicas podem ser utilizadas para a purificao da cafena obtida?
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7) Calcule o rendimento.
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PRTICA No 16
Sntese do cido acetilsaliclico
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

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2) Faa uma reviso nas tcnicas de aquecimento utilizadas na sntese orgnica.
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3) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
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4) Quais os cuidados devem ser observados ao trabalhar com os reagentes utilizados nesta sntese?
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5)

Fornea o mecanismo da reao.

6)

Faa o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

Material: Balana, bquer, pisseta com gua, basto de vidro, provetas (10mL e 100mL), funil de bchner, kitasato, mufas, garras,
suportes, trompa de vcuo, papel de filtro, esptula, balo, termmetro, banho-maria, pipeta.
Reagentes: cido saliclico, anidrido actico, cido sulfrico, cido actico.
Introduo:
O cido acetilsaliclico, comercialmente conhecido como aspirina um composto simples que possui um largo espectro
de ao biolgica: Alm de ser um analgsico eficaz, antipirtico, anti-inflamatrio, anti-reumtico e atua na preveno de
cogulos arteriais, devido sua ao anti-coagulante, prevenindo ataques cardacos e enfartos. um dos frmacos mais utilizados
em todo o mundo. Esta substncia pode ser obtida a partir das folhas do salgueiro (Salix alba), espcie utilizada desde a antigidade
por suas propriedades analgsica e anti-pirtica.
Na verdade, o agente farmacologicamente ativo o cido saliclico. Entretanto, devido presena dos grupos hidroxila e
carboxilato em sua estrutura, esta substncia pode provocar irritaes na mucosa oral, esfago e estmago, podendo causar
hemorragias. O cido acetilsaliclico, mostrou-se menos irritante. Aps ser ingerida, esta substncia hidrolisada, fornecendo o
cido saliclico, que ento absorvido.
COOH
COOH

OH

OCOCH3

cido saliclico
cido acetilsaliclico
Parte Experimental:
Em um balo de fundo redondo, colocar 10g de cido saliclico e 15g (14mL) de anidrido actico. Adicionar 5 gotas de
cido sulfrico concentrado e agitar o balo at que a mistura seja completa. Aquecer a mistura em banho-maria, a 50-60oC, sob
agitao, por cerca de 15 min. Deixar a mistura esfriar e agitar ocasionalmente. Adicionar 150mL de gua, agitar bem e filtrar a
vcuo.
Recristalizar o cido acetilsaliclico impuro, com uma mistura de volumes iguais de cido actico e gua. Filtrar a vcuo,
tentando retirar o mximo da gua possvel.
Com uma esptula, transferir os cristais para uma folha de papel de filtro, ou papel-toalha, pressionando-a para secar o
slido. Secar.

PRTICA No 16
Sntese do cido acetilsaliclico
Estudante:__________________________________________________________
1) Como podemos detectar, no meio de reao, se ainda h cido saliclico sem reagir ?
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2) Calcular o rendimento da reao.
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3)

O cido saliclico pode irritar o estmago. O que normalmente feito na formulao deste frmaco que reduz este efeito
colateral?
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4) Qual o propsito da adio do cido sulfrico na preparao da aspirina? Outro cido pode ser usado?
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5) O que pode acontecer ao rendimento da reao, se o produto obtido no estiver completamente seco?
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PRTICA No 17
Sntese do benzoato de metila
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

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2) Faa uma reviso na tcnica de separao de lquidos imiscveis.
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3) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

4) Fornea o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

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Material: 2 bales de fundo redondo de 250mL; provetas de 100 e 50mL; condensador de refluxo; termmetro; aparelhagem para
destilao simples; funil de separao; erlenmeyer de 150mL; condensador de ar.
Reagentes: cido benzico; metanol; diclorometano; H2SO4; MgSO4 anidro; soluo saturada de NaHCO3.
Introduo:
O mtodo mais utilizado para a preparao de steres a reao entre cidos carboxlicos e seus derivados e lcool. Os
steres mais simples so normalmente preparados pela esterificao de Fischer que consiste na reao de um cido carboxlico
com um lcool em presena de um cido mineral:

O
RC

OH

H3O

RC
OH

OH

R C OH

OH
H
R C OH

HOR'

OR'

OH

R'OH

O
+

RC

H3O

OR'

OH
RC

H2O

OR'

A reao reversvel e para obter um rendimento satisfatrio, necessrio deslocar o equlbrio no sentido da formao
do ster. Para este fim, pode ser utilizado excesso de um dos reagentes ou a remoo de um dos produtos do meio.
Uma das formas de remover um dos produtos do meio de reao a destilao. A destilao simples consiste numa tcnica de
separao de lquidos que possuem ponto de ebulio abaixo de 150 oC a 1 atm, de outros lquidos cujo ponto de ebulio difere dos
primeiro em mais de 25 oC, ou de impurezas no volteis..
A fonte de aquecimento pode ser um bico de gs, manta aquecedora ou banho de vapor. O frasco contendo o material a
ser destilado no deve ser muito grande, pois aumenta a perda do produto, diminuindo o rendimento; ou to pequeno, que no caba
todo o material a ser destilado.
Um ponto importante a ser observado que o nvel do material a ser destilado no deve ultrapassar o meio do balo, para
evitar que material no destilado, quando entrar em ebulio, alcance o condensador. O balo nunca deve ser aquecido a secura.
O bulbo do termmetro deve estar na altura da sada do vapor para o condensador.
A destilao a temperaturas superiores a 140 oC geralmente deve ser conduzida com condensador refrigerado a ar, para
evitar coque trmico decorrente da diferena de temperatura entre o vapor do destilado e a gua corrente que normalmente
utilizada.
Parte Experimental:
No balo de fundo redondo, colocar 20g de cido
benzico, 70mL de metanol e 2mL de cido sulfrico. Aquecer
sob refluxo por 2 horas. Destilar o excesso de metanol
(CUIDADO!!). Deixar esfriar o resduo do balo e vert-lo em
250mL de gua. Transferir a mistura para o funil de separao.
Extrair o produto com 10mL de diclorometano, por 3 vezes.
Desprezar a camada aquosa e lavar a frao orgnica com gua,
depois com a soluo de bicarbonato de sdio (at cessar o
desprendimento de CO2) e por fim com gua novamente.
Transferir a frao orgnica para um erlenmeyer
seco e adicionar cerca de 2g de sulfato de magnsio anidro.
Filtrar. Destilar o filtrado utilizando um condensador de ar.
Recolher a frao que destila a 198-200 oC (rendimento
esperado: 60-70%).

Destilao simples

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PRTICA No 17
Sntese do benzoato de metila
Estudante:___________________________________________________________
1) Qual a funo do banho de leo?
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2) Por que so adicionadas prolas de vidro mistura de reao?
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3) Quando e por qu deve ser utilizado o condensador a ar?
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4) Por que a destilao simples no utilizada na separao de lquidos de pontos de ebulio prximos?
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5)

Por que perigoso aquecer um composto orgnico em um sistema totalmente fechado?

6) Esquematize uma montagem para aquecimento sob refluxo.

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__________________________________________________________________________________________________________
o
______PRTICA N 18

Sntese do nitrobenzeno
Trabalho pr-laboratrio:

1)

Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.

2)

Qual(ais) o(s) objetivo(s) desta prtica?

3)

Fornea o mecanismo da reao ocorrida.

4)

Quais os cuidados devem ser observados ao trabalhar com os reagentes utilizados nesta sntese?

5)

Faa o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

Material: Balana, bquer, pisseta com gua, basto de vidro, provetas (50mL), funil de haste, funil de separao, mufas, garras,
suportes, algodo, esptula, balo, termmetro, banho-maria, condensador.
Reagentes: cido ntrico, cido sulfrico, benzeno, cloreto de clcio anidro, soluo de NaOH 10%
Introduo

Apesar de serem compostos muito estveis, os hidrocarbonetos aromticos podem ser submetidos a reaes de
substituio eletroflica aromtica. Assim, o cido ntrico em presena de cido sulfrico, fornece o eletrfilo necessrio para que a
reao ocorra.
As reaes de nitrao geralmente so realizadas em condies brandas, para evitar perda do material, devido ao carter
oxidante dos cidos envolvidos.
NO2
HNO3
H2SO4

Parte Experimental

Em um balo de fundo redondo de 500mL, adicionar, em pequenas pores e agitao constante 35 mL de HNO3 e 40
mL de H2SO4 (CUIDADO!! Os vapores liberados so extremamente txicos e podem levar morte). Manter a mistura de reao
resfriada, para que a temperatura do sistema no ultrapasse 60 oC. Adicionar 30 mL de benzeno , em pequenas pores, com
agitao constante e mantendo o sistema resfriado. Adaptar um condensador (sem gua) no balo e aquecer o sistema, em banhomaria, a aproximadamente, 60 oC, por 45 min. Agitar o balo vigorosamente a cada 10 minutos, aproximadamente.
Verter a mistura de reao em um erlenmeyer contendo 50 mL de gua fria, agitando sempre. Deixar a mistura em
repouso por uma semana.
Transferir a camada orgnica para um funil de separao de 500mL e lavar o produto com 50 mL de gua, 50 mL de
soluo de NaOH 10% e 50 mL de gua.
Transferir o nitrobenzeno para um erlenmeyer contendo cerca de 5g de CaCl2 anidro. Filtrar em algodo. Destilar o
produto, utilizando um condensador de ar e coletar a frao destilada entre 205 210 oC (CUIDADO!! No deixar o balo secar,
pois pode haver resduo de m-dinitrobenzeno e outros nitrocompostos, que so explosivos.) Manipular o nitrobenzeno com cuidado
pois muito txico.
Observaes relevantes

PRTICA No 18
Sntese do nitrobenzeno

Estudante:__________________________________________________________
1)

Por que necessria a adio do cido sulfrico concentrado mistura de reao?

2)

Por que necessrio lavar o produto obtido?

3)

Por que a temperatura do sistema no pode ultrapassar 60 oC?

4)

Que subprodutos podem ser formados durante a reao?

5)

Por que foi utilizado um condensador a ar?

6)

Para que utilizado o nitrobenzeno?

6) Calcular o rendimento da reao.

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__________________________________________________________________________________________________________
____

PRTICA No 19
Preparao e purificao da anilina
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
2) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
3) Quais os cuidados devem ser tomados ao trabalhar com o nitrobenzeno?
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
4) Pesquise sobre a toxicidade de cada um dos reagentes utilizados neste experimento.
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________

5)

Fornea o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
Material: Suporte, garras, anel, mufas, bico de gs, balo de 500mL, condensador de refluxo, mangueiras de ltex, provetas de
20mL e de 100mL, funil de decantao, bquer de 500mL, erlenmeyers de 250mL, funil, basto, tela de amianto.
Reagentes: Nitrobenzeno, estanho granulado, HCl, soluo de NaOH 15 M , soluo de NaCl 20%, ter etlico, NaSO44 anidro.
Introduo:
Vrios grupos funcionais podem sofrer reduo. Os nitrocompostos,, por exemplo, podem ser reduzidos a aminas, em
presena de zinco, estanho ou ferro, em meio cido. Quando a reao ocorre em condies mais suaves, pode ser interrompida,
dando origem a nitrosamina.
O nitrobenzeno , nestas condies, fornece anilina, um leo incolor, utilizada na sntese de medicamentos, na indstria de
resinas, vernizes, etc.
NO2

NH2
Sn
HCl

Parte Experimental:
Em um balo de fundo redondo de 500mL equipado com um condensador a ar, colocar 10mL de nitrobenzeno, e 10g de
estanho granulado (trabalhar em capela!). Adicionar, lentamente, 120 mL de HCl, em poes de 10 mL (CUIDADO!), com agitao
constante. Aquecer a mistura em banho-maria, durante 1 h Esfriar a mistura de reao e adicionar a soluo de NaOH, lentamente,
mantendo a mistura de reao temperatura ambiente. A anilina se separa da soluo alcalina, sob a forma de um leo.
Destilar a anilina por arraste de vapor. Saturar o destilado com soluo de NaCl a 20% e transferir a mistura para um
funil de separao. Extrair a anilina com 3 pores de 30 mL de ter etlico. Reunir as solues etreas obtidas e secar com Na2SO4
anidro. Destilar o ter (CUIDADO!) e calcular o rendimento.
Observaes relevantes:
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__________________________________________________________________________________________________________
o

PRTICA N 19

Preparao e purificao da anilina

Estudante:___________________________________________________________
1)

Fornea o mecanismo da reao.

__________________________________________________________________________________________________

2) Para que utilizada a soluo de NaCl?

__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
3) Para que utilizado o estanho?
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__________________________________________________________________________________________________________

4)

Por que a anilina solvel em soluo aquosa de cido clordrico?

5)

Quais so os cuidados indispensveis quando ter etlico destilado?

6)

Fornea exemplos, na indstria, para uso da anilina.

________

PRTICA No 20
Preparao e purificao da acetanilida
Trabalho pr-laboratrio:

6) Qual(ais) o(s) objetivo(s) desta prtica?

__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
7) Quais os cuidados devem ser tomados ao trabalhar com anilina?
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
8) Qual o ponto de fuso da acetanilida?
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
9) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________

10) Fornea o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
Material: Suporte, garras, anel, mufas, bico de gs, balo de 250mL, condensador de refluxo, mangueiras de ltex, provetas de
20mL e de 100mL, funil de bchner, kitasato, trompa de vcuo, papel de filtro, tesoura, bquer de 500mL, erlenmeyers
de 250mL, funil, basto, tela de amianto.
Reagentes: Anilina, anidrido actico, cido actico glacial, gua, carvo ativado.
Introduo:
Os derivados acetilados de aminas aromticas podem ser preparados por reao destas com o anidrido actico ou cido
actico ou a mistura de ambos. As aminas primrias reagem prontamente com o anidrido actico, formando o derivado monoacetilado:

C6H5NH2 + (CH3CO)2O

C 6H5NHCOCH3 + CH3COOH

Se o aquecimento for prolongado e um excesso de anidrido actico empregado, pode ocorrer a formao de derivados diacetilados:
O
H

C CH3

N
C CH3

C CH3

+ (CH3CO)2O

+ CH3COOH

A produo de derivados di-acetilados facilitada pela preparao de substituintes do ncleo aromtico na posio orto:
por exemplo, obtm-se um excelente rendimento quando a o-toluidina aquecida com um excesso de anidrido actico:
CH3

CH3
NH2
+ 2 (CH3CO)2O

C CH3
N
C CH3

+ 2 CH3COOH

Entretanto, os derivados di-acetilados geralmente so instveis em presena de gua, sofrendo hidrlise e formando o
composto mono-acetilado. Assim, quando o derivado di-acetilado recristalizado em solvente aquoso (lcool diludo, por exemplo),
somente o derivado mono-acetilado obtido como produto final.
Parte Experimental:
Em um balo de fundo redondo de 250ml equipado com um condensador de refluxo, colocar 10mL de anilina, 10mL de
anidrido actico e 10mL de cido actico glacial. Aquecer a mistura durante 30 min. e ento transferir o lquido para um bquer de
500mL, contendo 250mL de gua fria, sob agitao constante. Depois de frio, filtrar o produto em funil de bchner, lavar com um
pouco de gua fria e secar.
Colocar a acetanilida obtida em um erlenmeyer de 250mL. Medir 100mL de gua, adicionar cerca de 30mL ao slido e
aquecer brandamente. Um leo incolor aparece; isto nada mais que uma soluo saturada de gua e acetanilida que pode existir
como fase separada em contato com a fase aquosa. Continuar adicionando pequena quantidade de gua dos 100mL originais,
mantendo a temperatura da soluo no ponto de ebulio at que o ltimo resduo de leo desaparea. Adicionar finalmente, mais
5mL de gua soluo. Deixar esfriar um pouco e adicionar de 0,5 a 1g de carvo ativado. A primeira poro deve ser adicionada
CUIDADOSAMENTE a fim de evitar que o material se projete. Finalmente, aquecer a mistura por um ou dois minutos
temperatura de ebulio.
Filtrar a soluo quente para remover o carvo. A soluo filtrada colocada num erlenmeyer e deixada em repouso.
Aps completa cristalizao, filtrar os cristais em funil de bchner, lavar com gua duas ou trs vezes e finalmente transferi-los para
um vidro de relgio, deixar secar e pesar. Calcular o rendimento da reao.
Observaes relevantes:
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________

PRTICA No 20
Preparao e purificao da acetanilida
Estudante:___________________________________________________________
7) Fornea o mecanismo da reao.
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8) Para que foi utilizado o carvo ativado?

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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
9) Para que so utilizadas as prolas de vidro?
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__________________________________________________________________________________________________________
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10) A reao de acetilao, principalmente de aminas aromticas, muito utilizada em sntese. Justifique.
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__

PRTICA No 21
Estudo da nitrao da acetanilida
Trabalho pr-laboratrio:

1) Qual(ais) o(s) objetivo(s) desta prtica?

__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
2) Faa uma reviso na tcnica de determinao do ponto de fuso.
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
3) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
__________________________________________________________________________________________________________
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4) Quais os cuidados devem ser observados ao realizar uma reao de nitrao?
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__
__________________________________________________________________________________________________________
________________________________________________________________________________________________________

5)

Qual o ponto de fuso da p-nitroacetanilida?

6) Por que esta reao no deve ser realizada com a anilina?

__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
7)

Quais os cuidados devem ser observados ao trabalhar com os reagentes utilizados nesta sntese?

8)

Fornea o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

Material: Suportes, garras, anis, bqueres de 1000, 250 e 125 mL, termmetros, basto, funil de bchner, kitasato, funil sem
cnula, erlenmeyers de 250mL, papel de filtro, vidros de relgio, esptula.
Reagentes: acetanilida, cido actico glacial, cido sulfrico, cido ntrico, etanol.
Introduo:
Compostos aromticos so em geral, pouco reativos, mas podem ser nitrados, usando uma mistura sulfo-ntrica. A reao
ocorre pela substituio do H do anel por um grupo nitro (NO2).
C6H6

+ HONO2

H2 SO4

C6H5NO2 + H2O

Compostos aromticos mono-substitudos podem ser nitrados em condies diferentes, dependendo das caractersticas do
grupo existente no anel. Assim, grupos desativadores, meta-orientadores, geralmente exigem condies mais enrgicas para a
nitrao, sendo necessrias temperaturas mais elevadas e concentraes mais altas de cidos. Por outro lado, grupos ativadores,
orto-, para- orientadores, indicam nitraes em condies mais brandas, sendo mesmo s vezes necessrio o resfriamento da reao.
Parte Experimental:
Num bquer de 125mL, pesar 10g de acetanilida seca e adicionar 10mL de cido actico glacial. Agitar bem e
acrescentar VAGAROSAMENTE, 20mL de cido sulfrico concentrado. Aps a mistura completa dos reagentes, resfriar o bquer
em um banho de gelo at que a temperatura esteja abaixo de 10 oC. Adicionar em seguida, LENTAMENTE, sem deixar haver
aquecimento excessivo, uma mistura de 4mL de cido ntrico e 3mL de cido sulfrico, ambos concentrados. Agitar ocasionalmente
a mistura durante 20 minutos e despejar em seguida em um bquer contendo 100mL de gua gelada. O precipitado amarelo que se
forma deve ser filtrado num funil de bchner.
Recristalizar este precipitado utilizando 20mL de etanol e filtrar novamente num funil de bchner. Pese num vidro de
relgio depois de seco. Determine o ponto de fuso.

PRTICA No 21
Estudo da nitrao da acetanilida
Estudante: __________________________________________________________
1) Fornea o mecanismo da reao que ocorreu durante o processo.
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________

2)

Por que a temperatura do sistema no deve ser maior que 50 oC?

3)

Por que a reao conduz, preferencialmente, formao do ismero para?

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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
o

PRTICA N 22

Bromao da acetanilida
Trabalho pr-laboratrio:

1) Qual o objetivo desta prtica?

__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
2) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
__________________________________________________________________________________________________________
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__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
3) Quais os cuidados devem ser observados ao trabalhar com os reagentes utilizados nesta sntese?
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
__________________________________________________________________________________________________________

4)

Fornea o planejamento do material a ser utilizado na reao.

Substncia

PM

massa /volume

mol

equivalentes

densidade

PF

PE

__________________________________________________________________________________________________________
__________________________________________________________________________________________________________
Material: Suportes, garras, anis, bqueres de 125 mL, esptula, basto, funil de bchner, kitasato, papel de filtro, vidros de
relgio.
Reagentes: acetanilida, cido actico glacial, bromato de potssio, soluo de cido bromdrico a 48%, soluo de bissulfito de
sdio a 10%, cido ntrico, etanol.
Introduo:
A bromao da acetanilida um timo exemplo da substituio eletroflica aromtica. Mas muitas das tcnicas
publicadas requerem a manipulao de bromo lquido ou solues contendo bromo (TXICO!!). Nesta tcnica, a manipulao
evitada pela gerao de bromo in situ, de acordo com a seguinte equao:

6H+ +5Br- + BrO3- 3Br2 +3H2O

A quantidade de bromo gerado determinada pela quantidade de bromato de potssio usado. Esta tcnica geral, para
compostos aromticos contendo substituintes doadores de eltrons, tais como acetamido, hidroxila e grupo ter. Para alguns
compostos tambm possvel a clorao, substituindo os reagentes por clorato de potssio e cido clordrico.
O

H
N

N
KBrO3, HBr
cido actico
Br

Parte Experimental:
Em um erlenmeyer, colocar 2g (1,5mmol) de acetanilida, 0,85g (0,5mmol) de bromato de potssio e 2mL de cido
actico glacial. Agitar a mistura rapidamente com um agitador magntico. Adicionar 3mL (2,6mmol) de cido bromdrico a 48%.
Haver a formao de cor alaranjada. Agitar a mistura por 30min. temperatura ambiente. Aps este tempo, verter a mistura de
reao em 100mL de gua gelada. Agitar a soluo por 15min. e filtrar em funil de bchner. Lavar o slido, primeiro com soluo
de bissulfito de sdio para destruir qualquer resduo de bromo; depois com gua. Retirar o mximo de gua.
Recristalizar o produto obtido com etanol a 95%. Os cristais de 4-bromoacetanilida so agulhas incolores de ponto de
fuso entre 170 e 171 oC.
Observaes relevantes:
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o

PRTICA N 22

Bromao da acetanilida
Estudante:___________________________________________________________
1) Como podemos observar o consumo de bromo, durante a reao?
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2)

Calcular o rendimento da reao.

3)

Fornea o mecanismo da reao de bromao.

4)

Se, como material de partida, tivesse sido utilizada a anilina, qual (ais) o(s) produto (s) seria (m) obtido (s). Justifique.

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Caderno de Qumica Orgnica Experimental

95

PRTICA No 23
Preparao de polmeros
Trabalho pr-laboratrio:
1) Qual(ais) o(s) objetivo(s) desta prtica?
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2) Cite exemplos de polmeros conhecidos (ao menos trs), mostrando parte de sua frmula estrutural.
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3) Relacione, sob a forma de itens numerados, as etapas a serem seguidas durante a prtica.
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Material: provetas de 10mL, bquer de 50mL, basto de vidro, balo de fundo redondo, condensador de refluxo, tubos de vidro.
Reagentes: soluo de formol 40%, anilina, fragmentos de estanho, cido clordrico 6M, fenol, soluo de NaOH 40%
Introduo:
A polimerizao um processo de formao de molculas de alto peso molecular a partir da combinao de diversas
molculas de menor tamanho, idnticas ou no, denominadas monmeros. Usualmente os monmeros possuem duas ou mais
funes qumicas em sua estrutura. Estas funes podem ser: ligaes mltiplas reativas (C=C, C=O, CC, etc.), hidroxilas,
carboxilas seus derivados, compostos heterocclicos (epxidos, lactamas, lactonas, etc.). O tamanho das cadeias e a possibilidade de
interligao entre elas fazem com que polmeros possuam propriedades fsicas e mecnicas prprias. A partir destas caractersticas
mecnicas, podem ser classificados como:
Elastmeros: polmeros que, temperatura ambiente, possuem uma boa elasticidade.
Plsticos: slidos temperatura ambiente, mas que em determinado estgio de seu processamento so fluidos, podendo ser
moldados.
Fibras: polmeros lineares, cujas cadeias so orientadas longitudinalmente.
Quanto fusibilidade, podem ser:
Termoplsticos: capazes de fundir-se por aquecimento e solidificar-se por resfriamento.
Termorrgidos: capazes de adquirir, por aquecimento ou outro tratamento, uma estrutura tridimensional, com ligaes
cruzadas, insolveis e no passveis de serem fundidos.
As reaes de polimerizao, na verdade, so reaes clssicas dos compostos orgnicos e podem envolver adio ou
condensao. A polimerizao por adio, tambm chamada de polimerizao em cadeia ou poli-adio, ocorre principalmente com
monmeros vinlicos ou que contenham ligaes mltiplas reativas. Pode ser radicalar ou inica, com mecanismos muito
semelhantes queles de reaes de adio. A reao envolve, basicamente, trs etapas:
Iniciao: ao monmero adicionado uma molcula iniciadora, dando origem a um intermedirio reativo.
Propagao: reaes sucessivas e rpidas onde so consumidas e produzidas mais espcies reativas.
Finalizao: interrupo da reao em cadeia, ou pelo consumo de material reativo, ou pela adio de uma espcie reativa
poro terminal da cadeia.

Caderno de Qumica Orgnica Experimental

96

As poli-adies so caracterizadas pelo crescimento rpido das cadeias. As macromolculas resultantes geralmente
possuem cadeias longas, formadas por unidades estruturais idnticas.
A polimerizao por condensao, geralmente ocorre entre grupos funcionais diversos dando origem a novas funes.
Assim, um cido policarboxlico pode reagir com uma diamina ou um diol, fornecendo uma poliamida ou um polister,
respectivamente. As reaes se processam de forma semelhante quelas entre molculas mono-funcionais. O crescimento da cadeia
lento e geralmente, depende da extrao , do meio de reao, dos subprodutos gerados (gua, amnia, etc.).
OH

OH
O

... etc.

C
H

Quando cada monmero possui apenas dois grupos funcionais, a cadeia formada linear, mas quando no monmero est
presente ao menos mais um grupo funcional, o polmero resultante ramificado.
Em 1909, L. Baekeland demonstrou que era possvel produzir plsticos com formol, em presena de cido ou base como
catalisador. Estes polmeros so denominados baquelite.
O nylon o nome genrico para polmeros de amida e foi preparado pela primeira vez por W. Carothers, no incio do
sculo. Estes polmeros so largamente utilizados na engenharia, devido a sua alta resistncia ao impacto e a abrasivos, bem como
na manufatura de fibras, com uma grande aplicao na indstria txtil e na fabricao de cordas de alta resistncia.
A resina de fenol/formaldedo utilizada, na fase solvel, em revestimentos. Aps resfriamento, passa a ser um polmero
termorrgido que pode ser empregado na fabricao de peas industriais eltricas, aparelhos de telefone, interruptores, etc.
OH

OH
H

OH
CH2

NaOH
C

CH2OH

CH2

H
OH
CH2OH
OH

CH2OH

CH2OH

OH
CH2

CH2

CH2OH

calor

OH
CH2

CH2

H2C

OH
CH2

H2C

CH2
OH

CH2
OH

Parte Experimental:
Parte 1: Obteno de nylon:
Em um bquer, adicionar 6,6mL de soluo de cido clordrico 6M a 3,4mL de anilina. Misturar bem. Observar. Deixar
a soluo em repouso, at que atinja a temperatura ambiente. Em outro bquer, colocar 5mL de soluo de formaldedo 40%
(formalina)e adicionar a soluo concentrada de cloreto de anilina (10mL) preparada anteriormente. Adicionar um pequeno
fragmento de estanho. Observar. Examinar o produto e anotar suas propriedades.
Parte 2: Sntese de resina de fenol-formaldeido:
Em um balo de 100mL, colocar 5g de fenol, 10mL de formaldedo e 0,6 mL da soluo de NaOH 40%. Adaptar um
condensador de refluxo e aquecer a mistura, em banho de leo, suavemente, at a ebulio. Durante o aquecimento, a mistura
adquire uma colorao vermelha e sua viscosidade aumenta.
Manter em ebulio por 1 hora. Aps este perodo a mistura torna-se to viscosa que as bolhas de ar permanecem presas.
Remover o aquecimento e verter imediatamente a massa viscosa em um tubo de vidro. Deixar esfriar. Ser obtido um slido branco,
opaco.
ATENO!!! Lavar imediatamente o balo com a soluo de NaOH a 40%, antes que o produto solidifique!
Colocar o tubo em uma estufa a 50 oC por uma hora e a 70 oC por 4 horas. Aps este tempo ser obtida uma massa dura e
rsea de plstico.
Observaes relevantes:
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Caderno de Qumica Orgnica Experimental

97

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o

PRTICA N 23

Preparao de polmeros
Estudante:________________________________________________
1) Proponha mecanismos de reao das snteses apresentadas nas Partes 1 e 2.
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Caderno de Qumica Orgnica Experimental

98

2) Descreva as caractersticas dos polmeros formados.

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Caderno de Qumica Orgnica Experimental

99

PRTICA No 24
Estrutura de compostos orgnicos: Utilizao de modelos moleculares I
Trabalho pr-laboratrio:
1) Qual(ais) o(s) objetivo(s) desta prtica?
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2) Escreva a frmula estrutural para os quatro compostos de frmula molecular C4H9Br.
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3) Escreva as frmulas estruturais possveis para a frmula molecular C3H8O
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4) Desenhar as frmulas estruturais do 1,4-dimetilcicloexano, mostrando todos os ismeros e confrmeros possveis.
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Caderno de Qumica Orgnica Experimental 100

5) O que so hidrognios equivalentes?

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6) Defina conformao.
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7) Defina configurao.
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8) Defina isomeria.
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Introduo:
Compostos orgnicos podem ter uma ilimitada variedade de composio, forma e estrutura. Enquanto a frmula molecular nos
informa sobre o nmero e tipos de tomos presentes em um composto, nada informa sobre a sua estrutura. A frmula estrutural
uma representao bidimensional e mostra a seqncia na qual os tomos esto conectados, bem como o tipo de ligao envolvido.
Entretanto, o modelo molecular tridimensional e assim, podemos utilizar modelos fsicos para os representar.
Parte Experimental:
Parte 1: Com os modelos fsicos, construir as estruturas dos compostos do item 1. Para cada uma, e utilizando o que for observado,
desenhar estruturas de Newmann para cada uma delas. Para o butano, fazer a anlise conformacional da molcula.
Parte 2: Construir os modelos para os ismeros possveis para a frmula molecular apresentada no item 2.
Parte 3: Construir modelos fsicos para o ciclopropano, ciclobutano, ciclopentano e cicloexano. Discutir, completamente, as
conformaes possveis para cada um deles. O anel rgido ou flexvel?
Parte 4: Construir os modelos para o item 3, fazendo, o mais completamente possvel, a anlise conformacional do
dimetilcicloexano. Com o modelo na conformao de cadeira, observe: quantos hidrognios so axiais? Quantos equatoriais?

1,4-

Observaes relevantes:
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Caderno de Qumica Orgnica Experimental 101

PRTICA No 24
Estrutura de compostos orgnicos: Utilizao de modelos moleculares I
Estudante:___________________________________________________________
1) Desenhe os confrmeros eclipsados e alternados para o propano, utilizando o modelo de cavalete.
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2) Um grupo substituinte na posio equatorial mais estvel que na axial. Justifique.

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Caderno de Qumica Orgnica Experimental 102

3)

Compare o modelo com o diagrama abaixo. Identifique as posies axiais e equatoriais.

H
H H

H
H

H
H
H

axial

H
equatorial

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Caderno de Qumica Orgnica Experimental 103

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o

PRTICA N 25

Utilizao de modelos moleculares II: Estereoqumica

Trabalho pr-laboratrio:
1) Qual(ais) o(s) objetivo(s) desta prtica?
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2) Faa uma reviso no conceito de isomeria.
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3) Apresente, sob a forma de um fluxograma, os tipos de isomeria existentes.
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Caderno de Qumica Orgnica Experimental 104

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Introduo:
Na Prtica no 24 foram observadas algumas variaes moleculares que podem ocorrer nos compostos orgnicos, como
por exemplo:
1-Isomeria constitucional: molculas podem ter a mesma frmula molecular mas arranjos de tomos diferentes.
a) Isomeria de cadeia: Ismeros estruturais onde as diferenas residem na ordem na qual os tomos esto conectados entre si.
EXEMPLO: Fornea os ismeros possveis para a frmula molecular C4H10

b)

Isomeria de posio: Ismeros estruturais onde as diferenas residem na localizao do grupo funcional.

EXEMPLO: Fornea os ismeros possveis para a frmula molecular C3H17Cl

2- Estereoisomeria: Molculas que possuem a mesma ordem de conexo de tomos, mas diferem no arranjo dos tomos no espao
tridimensional.
a) Isomeria E/Z (semelhante isomeria cis-trans): Molculas diferem entre si devido geometria de substituio em torno da
ligao dupla carbono-carbono. D origem a diasteroismeros.
EXEMPLO: Fornea os ismeros possveis para a frmula molecular C4H8.

b)

Enantimeros: Par de molculas que possuem a mesma conectividade, so imagens especulares uma da outra, mas no se
superpem. Possuem ao menos um estereocentro e no possuem plano de simetria.

EXEMPLO: Fornea os ismeros possveis para a frmula molecular CHClBr

Caderno de Qumica Orgnica Experimental 105

Parte Experimental:
Parte 1: Construa os modelos dos ismeros obtidos no exemplo 2b. Este modelo possui um plano de simetria? Que tipo de isomeria
existe entre eles? Desenhe projees de Fisher para cada um deles.

Parte 2: Construa modelos para o cido tartrico. Quantos estereoismeros so possveis? Quantos estereocentros existem? Que
tipo de estereoisomeria existe entre eles? A molcula quiral ou aquiral? Fornea a nomenclatura para os compostos.

Parte 3: Considere o cido lctico: CH3CH(OH)COOH. Desenhe projees de Fisher para cada um estereoismero possvel.
Fornea a nomenclatura adequada.

Caderno de Qumica Orgnica Experimental 106

Parte 4: Considere o 3-cloro-2-hidroxi-2-penteno. Fornea os estereoismeros possveis. Que relao existe entre eles? Fornea a
nomenclatura adequada.

Parte 5: Considere o 1-metilcicloexeno. Fornea os estereoismeros possveis. Que relao existe entre eles. Fornea a
nomenclatura adequada.

Caderno de Qumica Orgnica Experimental 107

PRTICA No 25
Utilizao de modelos moleculares II: Estereoqumica
Estudante:___________________________________________________________
1) O que plano de simetria?
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2) Qual a diferena entre diasteroismeros e enantimeros?
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3) No que consiste um composto meso?
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Caderno de Qumica Orgnica Experimental 108

4) No que consiste um estereocentro?

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5) No que consiste um composto quiral?
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Caderno de Qumica Orgnica Experimental 109

NDICE
Introduo i
ndice

1)
2)
3)
4)
5)
6)
7)
8)
9)
10)
11)
12)
13)
14)
15)
16)
17)
18)
19)

BIBLIOGRAFIA

_ Reversed Phase Chromatography Principles and Methods.. Amersham Pharmacia biotech Vstra Aros Tryckeri. Snits &
design AB. 1997. 89p.
ALLINGER, N.L., CAVA, M.P., JOGH, D.C., JOHNSON, C.R. LEBEL, N.A., STEVENS, C.L. Qumica Orgnica. 2 ed. Rio
de Janeiro: Guanabara Dois, 1982. 967p.
ANWAR, J., NAGRA, S.A., NAGI, M. Thin-Layer Chromatography: Four Simple Activities for Undergraduate Students.
Journal of Chemical Education 73(10):977-979. 1996.
BETTELHEIM, F.A. & LANDESBERG, J.M. Laboratory Experiments for Introduction to Organic & Biochemistry. Fort
Worth: Saunders Golden Publishing, 1997. 320p.
BORGFORD, C.L. & SUMMERLIN, L.R. Chemical Activities: Teacher Edition. Washington, D.C.: American Chemical
Society, 1988. 330p.
DOBREV, A.A. "Course Thesis" as End of the Laboratory Experimental Program. Journal of Chemical Education 73(9):856857. 1996.
HERMANN, C.K.F. First Day in Organic Lab. Journal of Chemical Education 73(9):852-854. 1996.
LEDERER, M. & LEIPZIG-PAGANI, E. Thin-Layer Chromatography Experiments That Illustrate General Problems in
Chromatography. Journal of Chemical Education 73(10):974-976. 1996.
MANO, E.B. & SEABRA, A.P. Prticas de Qumica Orgnica. 3a Ed. So Paulo: Editora Edgard Blcher Ltda. 1987.246p.
MARX, J. Organic Chemistry Laboratory Supplement. Dubuque: Kendall/Hunt Publishing Company, 1995. 64p.
MCMURRY, J. Qumica Orgnica 4ed. Rio de Janeiro Livros Tcnicos e Cientficos Editora S.A. 1997. 2v.
NEVES, H.J.C. Manual de Trabalhos Prticos em Qumica Orgnica. http://helium.dq.fct.unl.pt/QOF/PQO/ , 1997.
ROGANA, E., PEREIRA J.A., FERREIRA, G.A.L. Orgnica Experimental para Vestibulandos. Belo Horizonte: Imprensa da
Universidade Federal de Minas Gerais. 1968. 81p.
SCHFER, W., KLUNKER, J., SCHELENZ, T., MEIER, T., SYMONDS A. Laboratory Experiments Chemistry. Gttingen:
PHYWE Systeme GMBH. 19-.520p.
SCHATZ, P.F. Bromination of Acetanilide. Journal of Chemical Education 73(3): 267-268. 1996.
SOARES, B.G., SOUZA, N.A., PIRES, D.X. Qumica Orgnica: Teoria e Tcnicas de Preparao, Purificao e
Identificao de Compostos Orgnicos. Rio de Janeiro: Editora Guanabara S.A. 1988. 322p.
SOLOMONS, T.W.G. Qumica Orgnica. 6 ed. Rio de Janeiro: Guanabara. 1996. 2v.
VOGEL, A.I. Qumica Orgnica: Anlise Orgnica Qualitativa. 3 ed. Rio de Janeiro: Ao Livro Tcnico S.A. 1971. 3v.
ZUBRICK, J.M. The Organic Chem Lab Survival Manual: A Student's Guide to Techniques - 4 ed. Nova Iorque: John Wiley
& Sons, Inc. 1997.382p.

ii

Umas poucas palavras introdutrias

1
Prtica no 1- Determinao do ponto de fuso de compostos orgnicos
5
Prtica no 2 - Purificao atravs da tcnica de recristalizao
9
Prtica no 3 - Purificao de substncias atravs da sublimao
13
Prtica no 4 - Anlise qualitativa orgnica 17
Prtica no 5 - Caracterizao de compostos orgnicos 21
Prtica no 6 - Identificao de lcoois e fenis
25
Prtica no 7 - Identificao de carboidratos 31
Prtica no 8 - Cromatografia em camada delgada
35
Prtica no 9 - Separao de pigmentos em plantas: Cromatografia em coluna e em papel 39
Prtica no 10 - Destilao por arraste de vapor
43
Prtica no 11 - Isolamento da cafena
47
Prtica no 12 Estudo das propriedades de cidos e steres
51
Prtica no 13 Extrao e identificao de cidos graxos
55
Prtica no 14 - Preparao e caracterizao do cloreto de t-butila 59
Prtica no 15 - Solvlise do cloreto de t-butila
53
Prtica no 16 - Sntese do cido acetilsaliclico
67
Prtica no 17 - Sntese do benzoato de metila
71
Prtica no 18 Sntese do nitrobenzeno
75
Prtica no 19 Preparao e purificao da anilina
79
Prtica no 20 - Preparao e purificao da acetanilida 83
Prtica no 21 Estudo da nitrao da acetanilida
87
Prtica no 22 - Bromao da acetanilida
91
Prtica no 23 - Preparao de polmeros
95
Prtica no 24 - Estrutura de compostos orgnicos: Utilizao de modelos moleculares I 99
Prtica no 25 - Utilizao de modelos moleculares II: Estereoqumica
103
Bibliografia
109
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Caderno de Qumica Orgnica Experimental 110

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ii

NDICE
Introduo ............................................................................................................................................................. i
ndice..................................................................................................................................................................... ii

Umas poucas palavras introdutrias ............................................................................................................... 1

Prtica no 1- Determinao do ponto de fuso de compostos orgnicos .................................................5
Prtica no 2 - Purificao atravs da tcnica de recristalizao ......................................................... 9
Prtica no 3 - Purificao de substncias atravs da sublimao ....................................................... 13
Prtica no 4 - Anlise qualitativa orgnica ................................................................................................... 17
Prtica no 5 - Caracterizao de compostos orgnicos ............................................................................. 21
Prtica no 6 - Identificao de lcoois e fenis ........................................................................................ 25
Prtica no 7 - Identificao de carboidratos.......................................................................................... 31
Prtica no 8 - Cromatografia em camada delgada .................................................................................. 35
Prtica no 9 - Separao de pigmentos em plantas: Cromatografia em coluna e em papel ........... 39
Prtica no 10 - Destilao por arraste de vapor ........................................................................................ 43
Prtica no 11 - Isolamento da cafena ....................................................................................................... 47
Prtica no 12 Estudo das propriedades de cidos e steres................................................................. 51
Prtica no 13 Extrao e identificao de cidos graxos....................................................................... 55
Prtica no 14 - Preparao e caracterizao do cloreto de t-butila ..................................................... 59
Prtica no 15 - Solvlise do cloreto de t-butila ........................................................................................ 53
Prtica no 16 - Sntese do cido acetilsaliclico ....................................................................................... 67
Prtica no 17 - Sntese do benzoato de metila.......................................................................................... 71
Prtica no 18 Sntese do nitrobenzeno...................................................................................................... 75
Prtica no 19 Preparao e purificao da anilina................................................................................... 79
Prtica no 20 - Preparao e purificao da acetanilida........................................................................ 83
Prtica no 21 Estudo da nitrao da acetanilida ................................................................................... 87
Prtica no 22 - Bromao da acetanilida...................................................................................................... 91
Prtica no 23 - Preparao de polmeros ................................................................................................... 95
Prtica no 24 - Estrutura de compostos orgnicos: Utilizao de modelos moleculares I............. 99
Prtica no 25 - Utilizao de modelos moleculares II: Estereoqumica ..............................................103
Bibliografia .......................................................................................................................................................109