Decreasing order of dehydration of the following alcohols is:
Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question
Decreasing order of dehydration of the following alcohols is:
- a
A > D > B > C
- b✓
B > D > C > A
- c
B > A > D > C
- d
D > B > C > A
B > D > C > A
Step 1: Factors governing ease of dehydration
Dehydration of alcohols involves loss of water to form an alkene. The rate depends on:
- Stability of the carbocation formed (for E1 mechanism) or ease of H abstraction (E2).
- More stable carbocation → faster dehydration.
- 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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