Question:
Which one of the following will most readily be dehydrated in acidic solution?
Which one of the following will most readily be dehydrated in acidic solution?
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Carbocation stability increases with resonance → adjacent carbonyl group enhances dehydration rate.
Updated On: Apr 16, 2026
- Secondary alcohol with carbonyl nearby
- Secondary alcohol
- Tertiary alcohol
- Diol
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The Correct Option is A
Solution and Explanation
Concept:
Dehydration in acidic medium proceeds via carbocation formation. Stability of carbocation determines ease of dehydration. Additionally, nearby functional groups can stabilize carbocation via resonance.
Step 1: Effect of carbonyl group.
A carbonyl group (\(C=O\)) adjacent to the carbocation can stabilize it through resonance and electron-withdrawing effects.
Step 2: Compare options.
• (A) Secondary alcohol with nearby carbonyl → extra resonance stabilization → most favorable
• (B) Secondary alcohol → only moderate stability
• (C) Tertiary alcohol → stable, but no additional resonance stabilization
• (D) Diol → follows different dehydration pathway
Step 3: Conclusion.
Due to resonance stabilization by the carbonyl group, option (A) undergoes dehydration most readily.
Step 1: Effect of carbonyl group.
A carbonyl group (\(C=O\)) adjacent to the carbocation can stabilize it through resonance and electron-withdrawing effects.
Step 2: Compare options.
• (A) Secondary alcohol with nearby carbonyl → extra resonance stabilization → most favorable
• (B) Secondary alcohol → only moderate stability
• (C) Tertiary alcohol → stable, but no additional resonance stabilization
• (D) Diol → follows different dehydration pathway
Step 3: Conclusion.
Due to resonance stabilization by the carbonyl group, option (A) undergoes dehydration most readily.
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