Question
Thu November 10, 2011 By: Pratibha Roy

An organic compound (A) with molecular formula C7H5N on hydrolysis with strong aqueous acid gives another compound (B) which is a monobasic, aromatic carboxylic acid. The compound (B) on reaction with ammonia gives a salt which on heating gives compound (C). The compound (C) undergoes Halfmann bromomide reaction to give aniline. Identify (A), (B) &(C) & write the chemical reactions involved.

Expert Reply
Thu November 10, 2011
A is C6H5 CN
 
B is C6H5COOH
 
C is C6H5CONH2
 
C6H5CN + H3O+  -----> C6H5COOH
 
Carboxylic acids react with ammonia to give ammonium salt whichon further heating at high temperature give amides.
 
C6H5COOH + NH3 ---> C6H5COONH2
 
Hoffmann developed a method for preparation of primary amines bytreating an amide with bromine in an aqueous or ethanolic solutionof sodium hydroxide. In
 
C6H5COONH2 + Br2 + 4NaOH ----> RNH2 + Na2CO3 + 2NaBr + 2H2O
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