Which of the following alcohols is most easil | vedclass

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(C) The dehydration of alcohols with concentrated ${H_2SO_4}$ proceeds via an $E1$ mechanism,which involves the formation of a carbocation intermediat

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$p-CH_3O.C_6H_4.CH(OH)CH_3$

Vedclass · Answer

(C) The dehydration of alcohols with concentrated ${H_2SO_4}$ proceeds via an $E1$ mechanism,which involves the formation of a carbocation intermediate. The rate of dehydration depends on the stability of the carbocation formed. In the given options,all are secondary benzylic alcohols. The stability of the resulting benzylic carbocation is influenced by the substituent present on the benzene ring. Electron-donating groups $(EDG)$ stabilize the carbocation,while electron-withdrawing groups $(EWG)$ destabilize it. The methoxy group $(-OCH_3)$ is a strong electron-donating group due to its $+M$ effect,which significantly stabilizes the carbocation. The nitro group $(-NO_2)$ and chlorine $(-Cl)$ are electron-withdrawing groups,which destabilize the carbocation. Therefore,$p-CH_3O.C_6H_4.CH(OH)CH_3$ forms the most stable carbocation and undergoes dehydration most easily.

Which of the following alcohols is most easily dehydrated with concentrated ${H_2SO_4}$?

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