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Question

The relative rate of acid catalyzed dehydration of following alcohols would be:


A
III > I > IV > II
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B
III > IV > I > II
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C
I > III > IV > II
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D
III > IV > II > I
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Solution

The correct option is A III > I > IV > II
Rate of acid catalyzed dehydration is directly proportional to the stability of carbocation.
The carbocations generated from the given compounds are:




(iii) will be dehydrated at the fastest rate as the carbocation is 3 and stabilised by the phenyl group.
(ii) will be dehydrated at the slowest rate as the carbocation is 2.
Between (i) and (iv), (i) has a faster rate because after an H shift, the resulting carbocation is more stable.

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