Question Details

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

Options

A

propylamine

B

butylamine

C

butanamide

D

α–bromobutanoic acid

Show Answer

Correct Answer :

Option A

propylamine

propylamine

Solution :

The correct option is propylamine.

Let us analyze the reaction sequence step-by-step:

Step 1: Formation of compound A
The starting material is 1-iodopropane (CH3-CH2-CH2-I). When treated with sodium cyanide (NaCN), a nucleophilic substitution (SN2) reaction occurs, where the cyanide ion (CN-) replaces the iodide ion (I-). This increases the carbon chain length by one carbon atom.
CH3CH2CH2I+NaCNCH3CH2CH2CN+NaI
Thus, compound A is butanenitrile (CH3-CH2-CH2-CN).

Step 2: Formation of compound B
Partial hydrolysis of the nitrile compound A in the presence of hydroxide ions (OH-) yields an amide. Under mild basic conditions, the nitrile group (-CN) is partially hydrolyzed to a primary amide group (-CONH2):
CH3CH2CH2CNPartial hydrolysisOH-CH3CH2CH2CONH2
Thus, compound B is butanamide (CH3-CH2-CH2-CONH2).

Step 3: Formation of major product C
When the primary amide butanamide (compound B) reacts with bromine (Br2) in the presence of sodium hydroxide (NaOH), it undergoes the Hoffmann bromamide degradation reaction. This reaction degrades the amide to a primary amine containing one carbon atom less than the starting amide by eliminating the carbonyl carbon as a carbonate ion (CO32-):
CH3CH2CH2CONH2+Br2+4NaOHCH3CH2CH2NH2+Na2CO3+2NaBr+2H2O
Thus, the major product C is propylamine (CH3-CH2-CH2-NH2).

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