Question:

Identify the major product from the following reaction sequence:

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AgCN gives isocyanides (R–NC), while KCN gives nitriles (R–CN). Hydrolysis of isocyanides leads to primary amines.
Updated On: Jun 20, 2026
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The Correct Option is B

Solution and Explanation

Step 1: Understand the nature of AgCN reagent.
Silver cyanide (AgCN) is a covalent cyanide reagent. Unlike KCN (which gives cyanide substitution via carbon attack), AgCN promotes nucleophilic attack through nitrogen due to its covalent character. Hence, AgCN leads to formation of isocyanide (R–NC) rather than nitrile (R–CN).

Step 2: Reaction with benzyl bromide.

Benzyl bromide undergoes nucleophilic substitution reaction with AgCN. Since AgCN is less ionic, the nitrogen end attacks the benzyl carbon, forming benzyl isocyanide: \[ C_6H_5CH_2Br \rightarrow C_6H_5CH_2NC \]

Step 3: Formation of isocyanide intermediate.

The intermediate formed is benzyl isocyanide (C\(_6\)H\(_5\)-CH\(_2\)-NC). This compound is unstable under acidic hydrolysis conditions.

Step 4: Acidic hydrolysis step (H\(_3\)O\(^+\)).

Isocyanides on hydrolysis undergo cleavage of the C≡N-type linkage, ultimately forming a primary amine along with formic acid derivatives. The key product formed from the organic fragment is benzylamine.

Step 5: Mechanistic interpretation.

Hydrolysis converts –NC group into –NH\(_2\) group under acidic conditions: \[ R-NC \xrightarrow{H_3O^+} R-NH_2 + HCOOH \] Thus benzyl isocyanide gives benzylamine as major product.

Step 6: Final verification.

Since the final stable organic product contains –NH\(_2\) group attached to benzyl carbon, the correct answer is benzylamine.
Final Answer: \[ \boxed{C_6H_5CH_2NH_2} \]
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