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Question

Chemistry Question on Chemical Reactions

Identify the major product C formed in the following reaction sequence:
product C

A

Propylamine

B

Butylamine

C

butanamide

D

α-bromobutane acid

Answer

Propylamine

Explanation

Solution

Step 1: Reaction with NaCN :

CH3−CH2−CH2−I+NaCN→CH3−CH2−CH2−CNCH_3 - CH_2 - CH_2 - I + NaCN \rightarrow CH_3 - CH_2 - CH_2 - CN (A)

Step 2: Partial hydrolysis of nitrile :

CH3−CH2−CH2−CN+H2O→CH3−CH2−CH2−CONH2CH_3 - CH_2 - CH_2 - CN + H_2O \rightarrow CH_3 - CH_2 - CH_2 - CONH_2 (B)

Step 3: Hofmann degradation :

CH3−CH2−CH2−CONH2+NaOH+Br2→CH3−CH2−CH2−NH2CH_3 - CH_2 - CH_2 - CONH_2 + NaOH + Br_2 \rightarrow CH_3 - CH_2 - CH_2 - NH_2 (C)

Thus, the major product is propylamine.