JEE Main · 2023 · Shift-IhardALCO-042

Decreasing order of dehydration of the following alcohols is:

Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question

Question

Decreasing order of dehydration of the following alcohols is: image

Options
  1. a

    A > D > B > C

  2. b

    B > D > C > A

  3. c

    B > A > D > C

  4. d

    D > B > C > A

Correct Answerb

B > D > C > A

Detailed Solution

Step 1: Factors governing ease of dehydration

Dehydration of alcohols involves loss of water to form an alkene. The rate depends on:

  1. Stability of the carbocation formed (for E1 mechanism) or ease of H abstraction (E2).
  2. More stable carbocation → faster dehydration.
  3. Order of carbocation stability: benzylic > tertiary > secondary > primary.

Step 2: Assign types

  • (A) Phenol: The C-O bond in phenol has partial double bond character (resonance). Phenol is very resistant to dehydration — the phenoxide C-O is essentially unsusceptible to typical E1/E2 conditions. Slowest/Hardest to dehydrate.

  • (B) Benzylic secondary alcohol (e.g., 1-phenylethanol): Forms stable benzylic carbocation → very easy to dehydrate. Fastest.

  • (D) Tertiary or highly branched alcohol: Forms tertiary carbocation → relatively easy. Second fastest.

  • (C) Secondary aliphatic alcohol (cyclohexanol): Forms secondary carbocation → moderate. Third.

Order: B > D > C > A

Key Points to Remember:

  • Phenol is the hardest to "dehydrate" in a normal sense — its C-O bond is strengthened by resonance.
  • Benzylic alcohols dehydrate most easily (form stable benzylic carbocations).
  • General dehydration ease: benzylic > 3° > 2° > 1° >> phenol.

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