JEE Main · 2023 · Shift-ImediumGOC-066

Correct order of acidity of protons marked A-D:

General Organic Chemistry (GOC) · Class 11 · JEE Main Previous Year Question

Question

Correct order of acidity of protons marked A-D: image

Options
  1. a

    \ceHC>HD>HB>HA\ce{H_C > H_D > H_B > H_A}

  2. b

    \ceHC>HD>HA>HB\ce{H_C > H_D > H_A > H_B}

  3. c

    \ceHD>HC>HB>HA\ce{H_D > H_C > H_B > H_A}

  4. d

    \ceHC>HA>HD>HB\ce{H_C > H_A > H_D > H_B}

Correct Answerb

\ceHC>HD>HA>HB\ce{H_C > H_D > H_A > H_B}

Detailed Solution

Step 1: Identifying Acidic Sites

  • \ceHC\ce{H_C}: Carboxylic acid proton (Strongest acid, pKa45pK_a \approx 4-5).
  • \ceHD\ce{H_D}: Benzylic/Alpha proton (Stabilized by resonance with ring and carbonyl).
  • \ceHA\ce{H_A}: Terminal alkyne proton (spsp hybridized Carbon, pKa25pK_a \approx 25).
  • \ceHB\ce{H_B}: Benzylic/Propargylic proton (sp3sp^3 Carbon, less acidic than spsp).

Step 2: Acidic Strength Order \ceHC>HD>HA>HB\ce{H_C > H_D > H_A > H_B}

Answer: (b)\boxed{\text{Answer: (b)}}

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