INTRODUCERE

Chimia Organica este ramura chimiei in care sunt studiati compusii

carbonului si reactiile lor. O mare varietate de clase de substante, cum ar fi

medicamente, materiale plastice, fibre naturale si sintetice, ca si

carbohidrati, proteine si grasimi sunt formate din molecule organice.

Chimistii organici determina structura moleculelor organice, studiaza

reactiile lor si elaboreaza proceduri de sinteza a compusilor organici. Chimia

organica a avut un profund efect in secolul 20:a imbogatit materialele

naturale si a sintetizat materiale artificiale care au imbunatatit medicina , au

crescut comfortul oamenilor.

Inceputul chimiei organice este asociat cu descoperirea, in 1828, de catre

chimistul german Friedrich Wöhler, ca substanta inorganica cianura de amoniu

poate fi convertita in laborator in uree, o substanta organica gasita in urina

animalelor. Inainte de aceasta descoperire chimistii credeau ca interventia

asa numitei "forte de viata" este necesara pentru a sintetiza substante

organice. Experimentul lui Wöhler a darmat bariera dintre substantele

organice si anorgance. Chimistii moderni considera compusii organici a fi cei

care contin carbon si un alt sau mai multe elemente, cel mai des hidrogenul,

oxigenul, azotul, sulful si halogenii, dar cateodata si alte substante.

 LEGATURI SI FORMULE ORGANICE

Formula moleculara a unui compus indica numarul fiecarui fel de atomi in

molecula acelei substante. Fructoza, sau sucul de struguri(C6H12O6), consta in

molecule continand 6 atomi de carbon, 12 atomi de hidrogen si 6 atomi de

oxigen. Pentru ca sunt cel putin 15 alti compusi care au aceeasi formula

chimica, pentru a distinge o molecula de alt, este folosita o formula structurala

pentru a arata aranjamentul spatial al atomilor.

Chiar si anliza care ne da procentajul de carbon, oxigen si hidrogen nu pot

distinge C6H12O6 de riboza, C5H10O5, un alt zahar in care proportiile

elementelor sunt aceleasi, adica 1:2:1.

Fortele care tin atomii uniti intr-o molecula sunt legaturile chimice, cae

sunt de trei tipuri: ionice, covalente si metalice. Legaturile ionice sunt

determinate de atractia sarcinilor de sens opus. Legaturile covalente sunt

formate de perechi de electroni comuni. Experimentul lui Wöhler(fig.1), de

exemplu a rezultat in schimbarea din legaturi ionice in cianura de amoniu in

legaturi covalente din uree. In cianura de amoniu, atractia dintre un grup de

5 atomi NH4+ purtand sarcina pozitiva si un grup de alti 3 atomi in CNO-,

purtand sarcina negativa constituie o legatura ionica. in gruparea dinnge from

ionic bonds in ammonium cyanate to covalent bonds in urea. In gruparea NH4+

,cle 4 linii -N spre H reprezinta legaturi covalente dar si ionice. La fel , in

gruparea CNO-, in molecula de uree reprezinta legaturi covalente.

Inmcalzirea cianurii de amoniu are ca rezultat rearanjarea legaturilor.

Proprietatea carbonului de a forma legaturi covalente nu este unica.

Legaturile dintre azot si hidrogen sunt si ele covalente.Totusi abilitatea

acestuia de a forma legaturi covalente cu alti atomi de carbon in lanturi sau

inele, il distinge de alte elemente. Alte elemente nu formeaza lanturi mai

mari de 8 atomi identici. Aceasta proprietate a carbonului, si faptul ca,

carbonul aproape totdeauna formeaza 4 legaturi cu alti atomi conteaza pentru

un numar foarte mare de compusi cunoscuti. Cel putin 80% din cele 5

milioane de compusi chimici, cunoscuti inca de la inceputul anilor '80 contin

carbon.

CLASIFICARI SI NOMENCLATURI

Consecintele proprietatii unice a carbonului se manifesta in cea mai simpla

clasa de substante organice, hidrocarburile.

A Alcanii

Copmusul-parinte al acestei familii este metanul, CH4. Urmatorii membri ai

familiri sunt etanul (C2H6), propanul (C3H8) si butanul (C4H10), asa ca formula

generala pentru fiecare membrual familiei este CnH2n+2.Pentru compusi care

contin mai mult de 4 atomi, sunt utilizate prefixe grecesti cu sufixul - ane la

numele compusilor (pentan, hexan, octan, s.a.m.d).

Numele de pentan, butan, etc totusi nu sugereaza singure structura

moleculara. De exemplu, din formula moleculara C4H10 se pot intelege doua

formule structurale diferite.Compusii cu aceeasi formule moleculare, dar

formule structurale diferite sunt numiti izomeri.In cazul butanului, nume

comune de izomeri sunt n-butan si izobutan.Ureea si cianura de amoniu sunt

si ei izomeri: sunt izomeri structurali ai formulei moleculare CH4 N2O.

Formula C8H18 are 18 izomeri si C20H42 are366319 izomeri

teoretici.Uniunea Internationala a Chimiei Pure si Aplicate (IUPAC) a cazut

de acord in 1890 la un sistem de nomenclatura si l-a revizuit ca sa

incorporeze noi descoperiri.

In sistemul de nomenclatura IUPAC cel mai lung lant de carbon este

numarat pentru a da lanturilor laterale cea mai mica suma. Cele 3 lanturi

laterale din fig. 4 sunt atomii de carbon 2,2 si 4; daca lantul ar fi numarat

in directia opusa, lanturile laterale ar fi 2,4 si 4. Atunci, numele de

trimetilpentan ar fi corect, pt ce din el rezulta cea mai mica suma.

 Alta familie de hidrocarburi, ciclanii, au un inel sau o structura ciclica; cel

mai mic inel contine 3 atomi de carboni.Ciclanii au formula chimica generala

CnH2n.

B Alchenele si Alcanii

Familia alchenelor, sau izomerii ciclanilor si alcanilor, cum mai este

numita, este reprezentata de formula generala CnH2n.Aceasta familie de

hidrocarburi este caracterizata de una sau mai multe legaturi duble intre

atomii de carbon.Propanul si ciclopropanul, de exemplu, sunt izomeri, cum sunt

1,3-dimetilciclohexanul si 3,4-dimetil-2-hexanul.Legaturile duble se intampla

in compusii ciclici.
 Chimistii folosesc de obicei o notatie prescurtata cand scriu formulele

structurale ai compusilor ciclici organici.Fiecare atom are, de la sine inteles

2,1 sau 0 atomi de hidrogen in legatura.

Alcanii sau acetilenele sunt a treia mare familie a hidrocarburilor si au

formula generala CnH2n-2 si contin mai putini atomi de hidrogen decat

alchenele

C Grupuri Functionale

Alti atomi, cum ar fi la clor, oxigen sau azot pot fi inlocuiti cu hidrogenul in

alcani.
 D Izomeri Optici si Geometrici

Natura tetraedica a formelor legaturilor carbonului dicteaza niste

proprietatiai compusilor organici. Cand 4 grupuri diferite de atomi sunt

atasate la un atom central de carbon , 2 molecule diferite pot fi construite in

spatiu. De exemplu, compusul acid lactic exista in doua forme , un fenomen

numit izomerism optic.Izomerii optici sunt legati in acelasi fal cum on obiect

si imaginea sa din oglinda sunt legate. O Oglinda plasata intre cele doua

structuri ar reflecta ca gruparile: CH3 din primul reflectand pozitia CH3-ului

din cealalta, OH reflectand OH, si tot asa.

Optical isomers have exactly the same chemical properties and all of the

same physical properties except one: the direction that each type of isomer

turns a plane of polarized light (see Optics). Dextro-lactic acid, or D-lactic

acid, turns the plane of polarized light to the right and levo-lactic acid, or

L-lactic acid, to the left. Racemic lactic acid (a 1:1 mixture of D- and L-

lactic acid that is found in sour milk) exhibits zero rotation because left and

right rotations cancel each other.

Double bonds in carbon compounds give rise to geometric isomerism (not

related to optical isomerism) if each double bond has different groups

attached. A molecule of 2-heptene, for example, may be arranged two ways

in space because rotation about the double bond is restricted. When the like

groups, hydrogen atoms in this case, are on opposite sides of the double

bonded carbon atoms, the isomer is called trans and when the hydrogens are

on the same side, the isomer is called cis.

E Saturation Compounds containing double or triple bonds are said

to be unsaturated. Unsaturated compounds can undergo addition reactions

with various reagents that cause the double or triple bonds to be replaced

with single bonds. Addition reactions cause unsaturated compounds to become

saturated. Although saturated compounds are generally more stable than

unsaturated compounds, two double bonds in the same molecule cause less

instability if they are separated by a single bond. Isoprene, the building

block for natural rubber, has this so-called conjugated structure, as does

retinal, a compound derived from vitamin A.

Complete conjugation in a six-membered carbon ring has a more profound

effect, a stabilizing influence so strong that the compound is no longer

unsaturated. Benzene, C6H6, and the family of cyclic compounds called

aromatic hydrocarbons, do not add the reagents that react with isoprene,

alkanes, and alkenes. In fact, the properties of aromatic compounds are so

different that a more appropriate symbol for benzene is the hexagon on the

extreme right of Fig. 13 rather than the other two. The circle inside the

hexagon suggests that the six electrons represented as three conjugated

double bonds belong to the entire hexagon and not to individual carbons at

the corners of the hexagon. Other aromatic compounds are shown in Fig. 14.
Cyclic molecules may contain atoms of elements other than carbon. The most

common so-called hetero atoms are sulfur (S), nitrogen (N), and oxygen (O),

although others-for example, boron (B), phosphorus (P), and selenium (Se)-are

known.

IV SOURCES OF ORGANIC COMPOUNDS

Coal tar was once the only source of aromatic and some heterocyclic

compounds. Petroleum was the source of aliphatic compounds that contain

such substances as gasoline, kerosene, and lubricating oil. Natural gas

supplied methane and ethane. These three categories of natural substances are

still the major sources of organic compounds for most countries. When

petroleum is not available, however, a chemical industry can be based on

acetylene, which in turn can be synthesized from limestone and coal. During

World War II, Germany was forced into just that position when it was cut off

from reliable petroleum and natural-gas sources.

Table sugar from cane or beets is the most abundant pure chemical from a plant

source. Other major substances derived from plants include carbohydrates

such as starch and cellulose, alkaloids, caffeine, and amino acids. Animals feed

on plants and other animals to synthesize amino acids, proteins, fats, and

carbohydrates.

V DETERMINATION OF STRUCTURE

The use of chemical reactions to identify the structures of organic compounds

has been replaced largely by instrumental methods since 1940. Infrared spectra

are used to identify functional groups, and ultraviolet spectroscopy can

distinguish aromaticity and certain kinds of unsaturation in a molecule. A

nuclear magnetic resonance (nmr) spectrum gives the largest amount of

information about the structure of a compound; infrared and ultraviolet spectra

complement rather than duplicate such data. Proton resonance spectroscopy is

sometimes used to determine the nature of the local environment of the

hydrogen atoms in a molecule and it can often simultaneously supply the ratios

of types of hydrogen. More recently, carbon-13 nuclear magnetic resonance

spectroscopy has been used to derive complementary information to the proton

data. Also, an X-ray spectrum may be necessary to determine three-dimensional

aspects of structure in a complex organic molecule. See Chemical Analysis.

VI PHYSICAL PROPERTIES OF ORGANIC

COMPOUNDS In general, covalent organic compounds are distinguished

from inorganic salts by low melting points and boiling points. The ionic

compound sodium chloride (NaCl), for example, melts at about 800° C (about
1470° F), but the strictly covalent molecule, carbon tetrachloride (CCl4), boils at

76.7° C (170° F). Between these temperatures an arbitrary line may be drawn at

about 300° C (about 570° F) to distinguish most covalent from most ionic

compounds. A large fraction of organic compounds melt or boil below 300° C,

although exceptions exist. Organic compounds generally dissolve in nonpolar

solvents (liquids that do not have localized electric charges) such as gasoline or

carbon tetrachloride, or solvents of low polarity such as alcohols, acetic acid,

and acetone. Organic compounds are often insoluble in water, a strongly polar

solvent.

Hydrocarbons have low densities, often about 0.8 compared to water, 1.0, but

functional groups may increase the densities of organic compounds to 1.0. Only

a few organic compounds have densities greater than 1.2, generally those

containing multiple halogen atoms.

Functional groups capable of forming hydrogen bonds generally increase

viscosity (resistance to flow) in molecules. For example, the viscosities of

ethanol, ethylene glycol, and glycerol increase in that order. These compounds

contain one, two, and three OH groups, respectively, which form strong

hydrogen bonds.

VII CHEMICAL REACTIONS Chemists ordinarily design

organic reactions to be carried out at optimum conditions for the particular

reaction in order to produce maximum yields. To do so necessarily means that

the chemist must be aware of desirable catalysts, whether or not the reaction is

reversible, and how to take advantage of equilibrium positions. As an example,

two different products may be obtained in sulfonating naphthalene (adding the

SO3H functional group to a naphthalene molecule) by taking advantage of the

reversibility of this reaction (Fig. 16).

At a temperature of 80° C (176° F) the rate of reaction at the á-position is faster

than the rate at the â-position. Consequently, a 91 percent yield of á-

naphthalenesulfonic acid can be obtained at 80°; at a higher temperature, the â-

isomer predominates. At 160° C (320° F) the á-isomer desulfonates more rapidly

than the â-form, so an 85 percent yield of â-naphthalenesulfonic acid, the more

stable isomer, is obtained.

Catalysts are frequently essential for rapid chemical reactions. Water, for

example, will not add to unsaturated compounds unless a small amount of a

strong acid (represented in Fig. 17 by H+) is present. See Acids and Bases;

Catalysis; Chemical Reaction.