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MCQMediumJEE 2025SN1 & SN2 Reactions

JEE Chemistry 2025 Question with Solution

The product B formed in the following reaction sequence is: C6H5CN→HCl(A)→AgCN(B)\text{C}_6\text{H}_5\text{CN} \xrightarrow{\text{HCl}} (A) \xrightarrow{\text{AgCN}} (B)

Reaction scheme with an aromatic substrate undergoing treatment with HCl to give intermediate A, followed by AgCN to give product B, asking the major product.
  • A
    First option shows an aromatic ring attached to a side chain bearing an isocyanide group at the terminal substituted carbon.
  • B
    Second option shows an aromatic ring attached to a side chain bearing an isocyanide group on the secondary carbon of the propyl substituent.
  • C
    Third option shows an aromatic ring attached directly to a secondary carbon bearing a cyano group and a methyl substituent.
  • D
    Fourth option shows an aromatic ring attached directly to a secondary carbon bearing an isocyanide group and an ethyl substituent.

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: The product B is to be identified from the sequence involving HCl followed by AgCN.

Find: The correct option for product B.

The solution states that the correct option is C.

From the provided explanation:

  1. In the first step, benzonitrile undergoes hydrolysis with HCl to form benzamide.
  2. In the second step, the intermediate reacts with AgCN to give phenyl isocyanate.

Using the conclusion stated in the solution, the final answer is taken as option C.

Therefore, the correct option is C.

Source Discrepancy Note

The question image and the textual explanation on the solution do not fully match each other. The solution text discusses C6H5CN\text{C}_6\text{H}_5\text{CN} converting to benzamide and then to phenyl isocyanate, while the embedded option figure corresponds to structural organic products and the page explicitly marks C as the correct option.

Because the

Extracted solution image associated with the explanation, showing the product representation referenced on the solution page.

Common mistakes

  • Assuming AgCN gives the same product pattern as KCN is incorrect. AgCN commonly favors formation through nitrogen-end participation, so the product type can differ from ordinary cyanide substitution. Always distinguish AgCN from ionic cyanide reagents.

  • Ignoring the reaction intermediate A leads to the wrong final product. First identify what HCl does to the starting compound, then apply the second reagent to that intermediate rather than to the original substrate.

  • Relying only on the textual reagent names without checking the option structures can cause confusion in structure-based questions. Match the mechanistic outcome carefully with the displayed structural options before choosing the answer.

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