MCQEasyJEE 2025Aldehydes & Ketones

JEE Chemistry 2025 Question with Solution

The product (P) formed in the following reaction is:

Starting aromatic compound containing one ketone, one aldehyde, and one ester group, shown before reaction conditions.
  • A
    Reaction arrow labeled with zinc amalgam and hydrochloric acid indicating Clemmensen reduction conditions for the substrate.
  • B
    Product label P shown after the reaction arrow, indicating the unknown product to be identified from given options.
  • C
    First product structure option among the given answer choices for the Clemmensen reduction reaction.
  • D
    Additional product structure option image continuing the set of answer choices shown for the reaction.

Answer

Correct answer:B

Step-by-step solution

Standard Method

Given: The substrate is treated with Zn-Hg\text{Zn-Hg} and HCl\text{HCl}.

Find: The correct product (P) formed in this reaction.

Clemmensen reduction converts aldehydes and ketones into the corresponding hydrocarbon groups under strongly acidic conditions, while the ester group remains unchanged.

From the given structure:

  • the ketone side chain is reduced to CH2-\text{CH}_2- in the side chain,
  • the aldehyde group is reduced to CH3-\text{CH}_3,
  • the ester group is not reduced.

So we must select the option in which the ketone becomes an alkyl side chain, the aldehyde becomes a methyl group, and the ester remains as an ester.

The solution states that Option (2) correctly matches this transformation.

Therefore, the correct option is B.

Functional Group Analysis

Given: A compound containing ketone, aldehyde, and ester groups is subjected to Clemmensen reduction.

Find: Which option represents the product.

Identify principle: Clemmensen reduction selectively reduces carbonyl groups of aldehydes and ketones in acidic medium.

Apply reaction rule:

R-CHOR-CH3\text{R-CHO} \rightarrow \text{R-CH}_3 R-CO-R’R-CH2-R’\text{R-CO-R'} \rightarrow \text{R-CH}_2\text{-R'}

The ester group remains unchanged under these conditions.

Evaluate options:

  1. Options showing alcohol formation are incorrect because Clemmensen reduction does not convert these groups into alcohols.
  2. The correct structure must retain the ester and remove the aldehyde and ketone oxygen atoms.
  3. The option identified in the provided solution is Option (2).

Therefore, the correct option is B.

Common mistakes

  • Mistake: Treating Clemmensen reduction as if it forms alcohols from carbonyl compounds. Why wrong: Zn-Hg/HCl\text{Zn-Hg/HCl} reduces aldehydes and ketones all the way to hydrocarbons, not alcohols. Do instead: replace the aldehyde by CH3-\text{CH}_3 and the ketone carbonyl by CH2-\text{CH}_2-.

  • Mistake: Assuming the ester group is also reduced. Why wrong: under standard Clemmensen conditions, the ester remains unchanged while aldehydes and ketones are reduced. Do instead: keep the ester functionality intact when choosing the product.

  • Mistake: Choosing the option by counting oxygen atoms without checking functional group identity. Why wrong: different oxygen-containing groups behave differently in this reaction. Do instead: inspect each carbonyl group separately and apply reaction selectivity.

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