Reaction mechanism explains the pathway

CONCEPT GENERAL ORGANIC CHEMISTRY through which an organic reaction takes

place and the various methods of
(TYPES OF ORGANIC REACTIONS purification of organic compounds are
based on their physical and chemical
AND METHODS OF PURIFICATION properties.

OF ORGANIC COMPOUNDS)

Substitution
Electrophilic Reactions
Substitution Reactions Involve the direct replacement
Brought about by electrophiles such as of an atom or a group of atoms by
H+, Cl+, R, SO3, BF3, AlCl3, FeCl3, SnCl4. another atom or group of atoms
SE1 : Unimolecular, first order, very rare in aliphatic
without any change in the Nucleophilic
remaining part of the Substitution Reactions
compounds. molecule.
l Some important examples are replacement of the metal
Brought about by nucleophiles such as H–, BH4–,
atom in an organometallic compound by hydrogen, AlH4–, Cl–, OH–, OR–, H2O, RNH2, RSH, ROR, etc.
decarboxylation of silver salt of carboxylic acid by bromine SN1 : Unimolecular, first order, two steps reaction and
and isotopic exchange of hydrogen for deuterium or proceeds by carbocation mechanism.
tritium . l Favoured by mild and low concentration of nucleophiles and

SE2 : Bimolecular, second order, very common in solvent of high polarity.

aromatic compounds. l Stability of carbocation is the rate determining factor.
l Catalysed by Lewis and Bronsted acids.
l Some important examples are nitration,
l Inversion and retention of configuration take place.
sulphonation, Friedel-Crafts
reaction etc. SN2 : Bimolecular, second order, one step reaction and proceeds
TYPES OF through transition state.
l Favoured by strong and high concentration of
ORGANIC nucleophiles and solvent of low polarity.
REACTIONS l Steric hinderance is the rate determining
factor.
l Not catalysed by any catalyst.
Elimination
Reactions
Involve loss of atoms or groups from
adjacent carbon atoms resulting in the Addition
formation of a p bond. Reactions
E1 reaction : Unimolecular and two steps reaction. Involve combination between two
l Carbocation is formed as intermediate. reacting molecules to give a single molecule
l Dehydration of 2° and 3° alcohols proceeds of the product.
by E1 process. l Typical reactions of compounds containing
E2 reaction : Bimolecular and one step reaction. double or triple bonds.
l Transition state is formed. l May be initiated by electrophiles, nucleophiles

l Dehydration of 1° alcohol or free radicals.

proceeds by E2 process. l The molecules containing C C or
C C are readily attacked by electro-
philes while molecules having C O
or C N are readily attacked
by nucleophiles.
Sublimation
I nv o l v e s t h e d i r e c t
conversion of a solid into
gaseous state on heating without Simple
passing through the intervening Distillation
Involves conversion of a liquid into Fractional
liquid state e.g., purification of Distillation
io dine, camphor, vapours by heating followed by
Involves repeated distillations
naphthalene etc. condensation of vapours.
and condensations using
l Commonly used for liquids which are fractionating column.
Crystallisation sufficiently stable at their boiling l Used when the difference in boiling
Based on the principle of points and contain non-volatile points of two liquids is not much e.g.,
different solubilities of a given impurities e.g., purification of separation of crude oil in petroleum
organic compound and its benzene, ethanol, industry into various useful
impurities in the same solvent e.g., fractions such as gasoline,
acetone etc. kerosene oil, diesel oil
separation of sugar from common etc.
salt by dissolving in hot
ethanol.
METHODS
OF Distillation
PURIFICATION OF Under Reduced
Pressure
ORGANIC Used to purify liquids having very
COMPOUNDS high boiling points and liquids
Differential which decompose at or below their
Extraction boiling points. e.g., separation of
Chromatography Involves shaking of the aqueous glycerol from spent lye in
Steam soap industry.
Inv o l v e s s e p a r at i on of solution of the organic compound in a
Distillation
components of a mixture by the separating funnel with a suitable solvent
which is immiscible with water but in Used to separate substances
differential movements of
individual components which organic compound is very highly which are steam volatile,
through a stationary phase soluble. immiscible with water and
under the influence of a l Used to recover organic compounds contain non-volatile impurities
mobile phase. from their aqueous solutions e.g., e.g., purification of essential
separation of benzoic acid. oils, turpentine oil etc.