In a set of reactions m-bromobenzoic acid gave a product D. Identify the product D.

4 2011 AIPMT-PRE AminesPreparation of Amines Medium
In a set of reactions m-bromobenzoic acid gave a product D. Identify the product D.
A -
B -
C -
D -

Detailed Solution


Step 1: thionyl chloride converts the carboxylic acid into the acid chloride: m-$BrC_6H_4COOH + SOCl_2 \rightarrow$ m-$BrC_6H_4COCl$ (B) $+ SO_2 + HCl$
Step 2: ammonia converts the acid chloride into the amide: m-$BrC_6H_4COCl + NH_3 \rightarrow$ m-$BrC_6H_4CONH_2$ (C) $+ HCl$
Step 3: with $Br_2$/NaOH the amide undergoes Hoffmann bromamide degradation, giving a primary amine with one carbon less: m-$BrC_6H_4CONH_2 + Br_2 + 4NaOH \rightarrow$ m-$BrC_6H_4NH_2$ (D) $+ Na_2CO_3 + 2NaBr + 2H_2O$
The ring bromine is not affected in any step.
Hence D is m-bromoaniline.

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