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Identify the major product C formed in the following reaction sequence:
$CH_3-CH_2-CH_2-I \xrightarrow{NaCN} A \xrightarrow[\text{Partial hydrolysis}]{OH^-} B \xrightarrow[Br_2]{NaOH} C \text{(major)}$
A
butanamide
B
alpha-bromobutanoic acid
C
propylamine
D
butylamine
Detailed Solution
$CH_3-CH_2-CH_2-I \xrightarrow{NaCN} CH_3-CH_2-CH_2-CN$ (A) (nucleophilic substitution)
$CH_3-CH_2-CH_2-CN \xrightarrow[Partial\ hydrolysis]{OH^-} CH_3-CH_2-CH_2-CONH_2$ (B)
$CH_3-CH_2-CH_2-CONH_2 \xrightarrow{NaOH/Br_2} CH_3-CH_2-CH_2-NH_2$ (C) (Hofmann bromamide degradation – one carbon less)
So the major product C is propylamine.