Which one of the following alcohols will unde | vedclass

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(C) The rate of acid-catalyzed dehydration of alcohols via the $E_1$ mechanism depends on the stability of the carbocation intermediate formed after t

Vedclass · Accepted Answer

Cycloprop$-2-$en$-1-$ol

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(C) The rate of acid-catalyzed dehydration of alcohols via the $E_1$ mechanism depends on the stability of the carbocation intermediate formed after the loss of water. $1$. $CH_2 = CH-OH$ forms a vinyl cation,which is highly unstable. $2$. Cyclopentanol forms a secondary cyclopentyl carbocation. $3$. Cycloprop$-2-$en$-1-$ol forms a cyclopropenyl cation. The cyclopropenyl cation is an aromatic system ($2\pi$ electrons,$H$ückel's rule $4n+2$ where $n=0$),making it exceptionally stable. $4$. $Me_2CHOH$ (isopropyl alcohol) forms a secondary isopropyl carbocation. Since the cyclopropenyl cation is aromatic,its formation is the most favorable,leading to the greatest ease of dehydration.

Which one of the following alcohols will undergo acid-catalyzed dehydration with the greatest ease by the $E_1$ mechanism?

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