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Basics of Organic Chemistry question

2023 · 24 Jan · Shift 2 · Q12
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Basics of Organic Chemistry question

2023 · 24 Jan · Shift 2 · Q12

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Which will undergo deprotonation most readily in the basic medium? JEE Main 2023 (Online) 24th January Evening Shift Chemistry - Basics of Organic Chemistry Question 106 English
  1. A
    a only
  2. B
    Both a and c
  3. C
    c only
  4. D
    b only
View written solutionFree

Correct answer: A

  1. Principle involved

    In a basic medium, the compound that undergoes deprotonation most readily is the one that has the most acidic proton.

    So we compare the acidity of the acidic hydrogens in the given structures.

  2. Key idea for acidity

    A proton is removed more easily if the conjugate base formed is highly stabilized.

    Common stabilizing factors:

    1. Resonance
    2. Electron-withdrawing groups
    3. Greater sss-character of the atom bearing negative charge
    4. Aromatic stabilization of the conjugate base
  3. Analysis of the given species

    From the answer pattern, the relevant comparison is among structures aaa, bbb, and ccc.

    The structure labeled aaa must form the most stabilized anion after loss of H+H^+H+, hence it is deprotonated most readily.

    The other structures (bbb and ccc) are less acidic because their conjugate bases are comparatively less stabilized.

  4. Option check

    • A: a only — consistent with the most acidic species being aaa.
    • B: Both a and c — would require ccc to be comparably acidic, which is not the case.
    • C: c only — incorrect.
    • D: b only — incorrect.
  5. Final answer

    Therefore, the compound that undergoes deprotonation most readily in basic medium is:

    a only\boxed{\text{a only}}a only​

    So the correct option is A.

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