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Question

The compound which gives the most stable carbonium ion on dehydration is:

A
CH3CHOHCH3
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B
(CH3)3COH
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C
CH2=CHCH2CH2OH
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D
CH3OH
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Solution

The correct option is B (CH3)3COH
The dehydration of tertiary alcohol proceeds via tertiary carbocation intermediate which is most stable.
(CH3)3COHtertiary alcohol+H+H2O(CH3)3+C3o carbocationmore stable
CH3CHOHCH3+H+H2OCH3+CHCH32o carbocationless stable
CH2=CHCH2CH2OH+H+H2OCH2=CHCH2CH21o carbocation(least stable)+
Decreasing order of stability of carbocation is tertiary>secondary>primary>methyl.

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