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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 Whler, 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 Whler 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(C 6H12O6), 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 Whler(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.

Alcanii

Copmusul-parinte al acestei familii este metanul, CH 4. 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 C 4H10 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 CH 4 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.

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.

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 Llactic 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.

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 naturalgas 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.

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 (CCl 4), 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 position is faster than the rate at the -position. Consequently, a
91 percent yield of -naphthalenesulfonic acid can be obtained at
80; at a higher temperature, the -isomer predominates. At 160
C (320 F) the -isomer desulfonates more rapidly than the -form,
so an 85 percent yield of -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.