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Aldehydes Ketones and Carboxylic Acids question

2022 · 29 Jun · Shift 1 · Q7
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Aldehydes Ketones and Carboxylic Acids question

2022 · 29 Jun · Shift 1 · Q7

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Given below are two statements : Statement I : The esterification of carboxylic acid with an alcohol is a nucleophilic acyl substitution. Statement II : Electron withdrawing groups in the carboxylic acid will increase the rate of esterification reaction. Choose the most appropriate option :
  1. A
    Both Statement I and Statement II are correct.
  2. B
    Both Statement I and Statement II are incorrect.
  3. C
    Statement I is correct but Statement II is incorrect.
  4. D
    Statement I is incorrect but Statement II is correct.
View written solutionFree

Correct answer: A

  1. Analyze Statement I

    Esterification of a carboxylic acid with an alcohol (Fischer esterification) proceeds by the following general mechanism:

    RCOOH+R′OH⇌H+RCOOR′+H2ORCOOH + R'OH \xrightleftharpoons[H^+]{} RCOOR' + H_2ORCOOH+R′OHH+​RCOOR′+H2​O

    In acid medium:

    • the carbonyl oxygen is protonated,
    • the alcohol attacks the carbonyl carbon as a nucleophile,
    • a tetrahedral intermediate is formed,
    • then elimination of water occurs,
    • giving the ester.

    This overall process is a nucleophilic acyl substitution: nucleophilic addition at the acyl carbon followed by elimination/substitution.

    So, Statement I is correct.

  2. Analyze Statement II

    Electron-withdrawing groups attached to the carboxylic acid increase the electrophilicity of the carbonyl carbon by pulling electron density away.

    As a result:

    • nucleophilic attack by the alcohol becomes easier,
    • the esterification reaction tends to proceed faster.

    Therefore, electron-withdrawing groups increase the rate of esterification.

    So, Statement II is correct.

  3. Evaluate the options

    • A: Both Statement I and Statement II are correct. ✅
    • B: Both incorrect. ❌
    • C: I correct, II incorrect. ❌
    • D: I incorrect, II correct. ❌

  4. Final Answer

    The correct option is:

    A\boxed{A}A​

  5. Comparison with stored correct answer

    Stored correct answer = A.

    My derived answer also = A.

    Hence, the answer agrees with the stored correct answer.

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