Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

An aromatic compound (A) on treatment with aqueous ammonia and heating forms compound (B) which on heating with Br2 and KOH forms a compound (C) of molecular formula C7H7NO.  

Identify the reaction taking place while converting compound B to compound C.

Options:

Cutis rearrangement 

Gabriel phthalamide reaction 

Hofmann Bromamide reaction 

Schmidt reaction 

Correct Answer:

Hofmann Bromamide reaction 

Explanation:

The correct answer is option 3. Hofmann Bromamide reaction.

Step 1:  To find out the structures of compound (B) and (C)

(i)Since compound (C) with molecular formula C6H7N is formed from compound (B) on treatment with Br2 + KOH (i.e., Hofmann Bromamide reaction), therefore, compound (B) must be an amide and (C) must be an amine. The only amine having molecular formula C7H7NO is C6H5NH2 (aniline).

(ii) Since (C) is aniline, therefore, the amide from which it is formed must be benzamide (C6H5CONH2). Thus, compound ‘B’ is benzamide.

The chemical equation showing the conversion of (B) to (C) is

 

Step2: To find out the structure of compound (A)

Since compound (B) is formed from compound (A) with aqueous ammonia and heating, therefore, compound (A) must be benzoic acid or benzenecarboxylic acid.