Question of 108
Q.Explain the following reactions:
(a) Carbylamine reaction
(b) Gattermann reaction
(c) HVZ (Hell-Volhard-Zelinsky) reaction
(d) Aldol condensation
Andhra Pradesh BieapBIEAP Intermediate Board 2024Subjective· 8mImportance★★★★★
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Start your 14-day free trial to unlock the full solution →Four named organic reactions: carbylamine (test for 1° amines), Gattermann (diazonium salt → aryl halide), HVZ (α-halogenation of acids), and aldol condensation (self-addition of carbonyl compounds with α-H).
- Carbylamine reaction (isocyanide test): When a primary amine (aliphatic or aromatic) is heated with chloroform (CHCl3) and alcoholic KOH, it forms an alkyl/aryl isocyanide (carbylamine), which has an extremely unpleasant, offensive smell: This reaction is specific to primary amines (both 1° aliphatic and 1° aromatic amines respond); secondary and tertiary amines do not give this test. It is therefore used as a qualitative test to distinguish primary amines from secondary and tertiary amines.
- Gattermann reaction: An aromatic diazonium salt, when treated with dry copper powder in the presence of the corresponding halogen acid (Cu/HCl or Cu/HBr), decomposes to give the aryl halide, releasing nitrogen gas: This is essentially a variant of the Sandmeyer reaction, using copper metal powder directly instead of cuprous salts (Cu2Cl2/Cu2Br2). It is a key method for introducing a halogen atom onto a benzene ring at a specific position (via the amine → diazonium → halide route), which cannot always be achieved by direct halogenation.
- HVZ (Hell–Volhard–Zelinsky) reaction: Carboxylic acids possessing an α-hydrogen atom react with chlorine or bromine (X2) in the presence of a small amount of red phosphorus to give the corresponding α-halo carboxylic acid: Mechanism outline: red phosphorus first reacts with X2 to form PX3, which converts the carboxylic acid to the corresponding acid halide; the acid halide (having enhanced enol content) is halogenated at the α-carbon, and the resulting α-halo acid halide then reacts with more carboxylic acid to regenerate the acid halide catalytically, giving the α-halo acid as product.
- Aldol condensation: …
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