Organic Chemistry Important Reagents-Edit

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Organic Chemistry – Specific Name Reactions
Sandmeyer Reaction
The Cl , Br and CN nucleophiles can easily be introduced in the benzene ring of benzene
diazonium salt in the presence of Cu(I) ion. This reaction is called Sandmeyer reaction.
Gatterman Reaction
Chlorine or bromine can be introduced in the benzene ring by treating the benzene diazonium
salt solution with corresponding halogen acid in the presence of copper powder. This is referred
as Gatterman reaction.
Note: The yield in Sandmeyer reaction is found to be better than Gattermann reaction.
Balz-Schiemann Reaction
When arenediazonium chloride is treated with fluoroboric acid, arene diazonium fluoroborate is
precipitated which on heating decomposes to yield aryl fluoride.
Finkelstein Reaction
Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with NaI in dry
acetone. This reaction is known as Finkelstein reaction.
Note: This reaction in forward direction can be favoured by precipitating NaX formed in dry
acetone (according to Le Chatelier’s principle).
Swarts Reaction
Heating an alkyl chloride/bromide in the presence of a metallic fluoride such as AgF, Hg2F2,
CoF2 or SbF3 gives alkyl fluorides. The reaction is termed as Swarts reaction.
Note: Finkelstein Reaction and Swarts Reaction are known as halogen exchange reaction.
Wurtz Reaction
Alkyl halides react with sodium in dry ether to give hydrocarbons containing double the number
of carbon atoms present in the halide. This reaction is known as Wurtz reaction.
Wurtz-Fittig Reaction
A mixture of an alkyl halide and aryl halide gives an alkylarene when treated with sodium in dry
ether and is called Wurtz-Fittig reaction.
Fittig Reaction
Aryl halides also give analogous compounds when treated with sodium in dry ether, in which
two aryl groups are joined together. It is called Fittig reaction.
Grade 12
Friedel-Crafts alkylation Reaction

When benzene is treated with an alkyl halide in the presence of anhydrous aluminium chloride,
alkylbenene is formed.
Note: Aromatic carboxylic acids do not undergo Friedel-Crafts reaction because the carboxyl
group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the
carboxyl group.
Friedel-Crafts acylation reaction
The reaction of benzene with an acyl halide or acid anhydride in the presence of Lewis acids
(AlCl3) yields acyl benzene.
Grade 12
Reimer-Tiemann Reaction
On treating phenol with chloroform in the presence of sodium hydroxide, a –CHO group is
introduced at ortho position of benzene ring resulting salicylaldehyde. This reaction is known as
Reimer - Tiemann reaction.
Kolbe’s Reaction
Phenol with sodium hydroxide gives sodium phenoxide ion which with carbon dioxide in acidic
medium results hydroxybenzoic acid (salicylic acid). This is known as Kolbe’s reaction.
Rosenmund Reduction
Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate. This
reaction is called Rosenmund reduction.
Stephen reaction
Nitriles are reduced to corresponding imine with stannous chloride in the presence of
hydrochloric acid, which on hydrolysis give corresponding aldehyde. This reaction is called
Stephen reaction.
Etard reaction
Chromyl chloride oxidizes methyl group to a chromium complex, which on hydrolysis gives
corresponding benzaldehyde. This reaction is called Etard reaction.
Gatterman – Koch reaction

When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the
presence of anhydrous aluminium chloride or cuprous chloride, it gives benzaldehyde or
substituted benzaldehyde. This reaction is known as Gatterman-Koch reaction.
Clemmensen Reduction
The carbonyl group of aldehydes and ketones is reduced to CH2 group on treatment with
zinc- amalgam and concentrated hydrochloric acid. This is known as Clemmensen
reduction.
Wolff Kishner Reduction

The carbonyl group of aldehydes and ketones is reduced to CH2 group on treatment with
hydrazine followed by heating with sodium or potassium hydroxide in high boiling solvent such
as ethylene glycol. This is known Wolff Kishner reduction.
Grade 12
Tollens’ test
On warming an aldehyde with freshly prepared ammoniacal silver nitrate solution (Tollens’
reagent), a bright silver mirror is produced due to the formation of silver metal. The aldehydes
are oxidised to corresponding carboxylate anion. The reaction occurs in alkaline medium.
Fehling’s test
Fehling reagent comprises of two solutions, Fehling solution A and Fehling solution B. Fehling
solution A is aqueous copper sulphate and Fehling solution B is alkaline sodium potassium
tartarate (Rochelle salt). These two solutions are mixed in equal amounts before test. On heating
an aldehyde with Fehling’s reagent, a reddish brown precipitate is obtained. Aldehydes are
oxidised to corresponding carboxylate anion. Aromatic aldehydes do not respond to this test.
Aldol reaction
Aldehydes and ketones having at least one α-hydrogen undergo a reaction in the presence of
dilute alkali as catalyst to form β-hydroxy aldehydes (aldol) or β-hydroxy ketones (ketol),
respectively. This is known as Aldol reaction. The name aldol is derived from the names of the
two functional groups, aldehyde and alcohol, present in the products.
Aldol condensation.
The aldol and ketol readily lose water to give α,β-unsaturated carbonyl compounds which are
aldol condensation products and the reaction is called Aldol condensation.
Cross aldol condensation:
When aldol condensation is carried out between two different aldehydes and / or ketones, it is
called cross aldol condensation. If both of them contain α-hydrogen atoms, it gives a mixture of
four products.
Cannizzaro reaction:
Aldehydes which do not have an α-hydrogen atom, undergo self oxidation and reduction
(disproportionation) reaction on treatment with concentrated alkali. In this reaction, one molecule
of the aldehyde is reduced to alcohol while another is oxidised to carboxylic acid salt.
Kolbe electrolysis
An aqueous solution of sodium or potassium salt of a carboxylic acid on electrolysis gives alkane
containing even number of carbon atoms.It is decarboxylation reaction. The reaction is known
as Kolbe electrolysis.
Grade 12
Hell-Volhard-Zelinsky (HVZ )reaction.

Carboxylic acids having an α-hydrogen are halogenated at the α-position on treatment with
chlorine or bromine in the presence of small amount of red phosphorus to give α-halocarboxylic
acids. The reaction is known as Hell-Volhard-Zelinsky reaction.
Gabriel phthalimide synthesis

Gabriel synthesis is used for the preparation of pure primary amines.
Phthalimide on treatment with ethanolic potassium hydroxide forms potassium salt of
phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the
corresponding primary amine.
Note: Aromatic primary amines cannot be prepared by this method because aryl halides do not
undergo nucleophilic substitution with the anion formed by phthalimide.
Grade 12
Hoffmann bromamide degradation reaction

An amide with bromine in an aqueous or ethanolic solution of sodium hydroxide gives primary
amines.
In this degradation reaction, migration of an alkyl or aryl group takes place from carbonyl carbon
of the amide to the nitrogen atom. The amine so formed contains one carbon less than that present
in the amide.
Carbylamine reaction
Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium
hydroxide form isocyanides or carbylamines which are foul smelling substances. This reaction is
known as carbylamines reaction or isocyanide test.
Note: Secondary and tertiary amines do not show this reaction and is used as a test for primary
amines.
Hinsberg’s Test
Benzenesulphonyl chloride (C6H5SO2Cl), which is also known as Hinsberg’s reagent, reacts

with primary and secondary amines to form sulphonamides.
The reaction of benzenesulphonyl chloride with primary amine yields N-ethylbenzenesulphonyl

amide. The hydrogen attached to nitrogen in sulphonamide is strongly acidic due to the presence
of strong electron withdrawing sulphonyl group. Hence, it is soluble in alkali.
In the reaction with secondary amine, N,N-diethyl- benzenesulphonamide is formed. Since N,

Ndiethylbenzene sulphonamide does not contain any hydrogen atom attached to nitrogen atom,
it is not acidic and hence insoluble in alkali.
Grade 12
Tertiary amines do not react with benzenesulphonyl chloride.

Note: This test is used for the distinction of primary, secondary and tertiary amines and also for
the separation of a mixture of amines. However, these days benzenesulphonyl chloride is
replaced by p-toluenesulphonyl chloride.
Coupling Reactions:
Benzene diazonium chloride reacts with phenol in which the phenol molecule at its para position
is
coupled with the diazonium salt to form p-hydroxyazobenzene. This type of reaction is known
as coupling reaction.
Similarly the reaction of diazonium salt with aniline yields p-aminoazobenzene.

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www.physicsgurukul.

Friedel-Crafts alkylation Reaction

Gatterman – Koch reaction

Wolff Kishner Reduction

Hell-Volhard-Zelinsky (HVZ )reaction.

Gabriel phthalimide synthesis

Hoffmann bromamide degradation reaction

Benzenesulphonyl chloride (C6H5SO2Cl), which is also known as Hinsberg’s reagent, reacts

The reaction of benzenesulphonyl chloride with primary amine yields N-ethylbenzenesulphonyl

In the reaction with secondary amine, N,N-diethyl- benzenesulphonamide is formed. Since N,

Tertiary amines do not react with benzenesulphonyl chloride.

Similarly the reaction of diazonium salt with aniline yields p-aminoazobenzene.

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