Which one of the following alcohols undergoes acid catalyzed dehydration to alkenes most readily?

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${(C H_{3})}_{2} C H C H_{2} O H$

${(C H_{3})}_{3} C O H$

$C H_{3} C H (O H) C H_{3}$

$C H_{3} C H_{2} C H_{2} O H$

answer is B.

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Detailed Solution

Alcohol which forms the more stable carbocation undergoes dehydration more readily. Among the given alcohols i.e., (CH₃)₂CHCH₂OH, (CH₃)₃COH, CH₃CH(OH)CH₃ and CH₃CH₂CH₂OH, tert-butyl alcohol [(CH₃)₃COH] forms more stable tert-butyl carbocation. Thus, it undergoes dehydration most readily.

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