MCQMediumJEE 2023Carboxylic Acids

JEE Chemistry 2023 Question with Solution

The major product PP formed in the following sequence of reactions is:

Reaction sequence starting from an aromatic carboxylic acid side chain compound treated with SOCl2, R-NH2, LiAlH4 and H3O+, asking for the major product among given structures.
  • A

    [Structure with OH and NHR]

  • B

    [Structure with Cl and OH]

  • C

    [Structure with CONHR]

  • D

    [Structure with CH2NHR]

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: The substrate is subjected to SOCl2\text{SOCl}_2, then R-NH2\text{R-NH}_2, then LiAlH4\text{LiAlH}_4, followed by H3O+\text{H}_3\text{O}^+.

Find: The major product PP after the full reaction sequence.

The sequence proceeds stepwise:

  1. SOCl2\text{SOCl}_2 converts the carboxylic acid group COOH-\text{COOH} into an acyl chloride COCl-\text{COCl}.

  2. Reaction with R-NH2\text{R-NH}_2 converts the acyl chloride into the amide CONHR-\text{CONHR}.

  3. LiAlH4\text{LiAlH}_4 reduces the amide CONHR-\text{CONHR} to the amine CH2NHR-\text{CH}_2\text{NHR}.

  4. H3O+\text{H}_3\text{O}^+ gives the acidic workup and protonates the intermediate.

Therefore, the final product contains CH2NHR-\text{CH}_2\text{NHR}. The correct option is D.

The solution states option (4) as the final product, even though one header shows C. From the reaction working, option (4) is chemically correct.

Common mistakes

  • Treating SOCl2\text{SOCl}_2 as if it directly reduces the acid is incorrect. It converts COOH-\text{COOH} to COCl-\text{COCl}. First identify the functional group interconversion before tracking the next reagent.

  • Stopping at the amide CONHR-\text{CONHR} is a common mistake. LiAlH4\text{LiAlH}_4 does not leave the amide unchanged; it reduces it further to CH2NHR-\text{CH}_2\text{NHR}.

  • Choosing the option based only on the inconsistent label in the provided header is wrong. The reaction mechanism shown in the explanation is the reliable basis, so the product must be the reduced amine.

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