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Q. Which one of the following alkylbromides undergoes most rapid solvolysis in methanol solution to give corresponding methyl ether?

Delhi UMET/DPMTDelhi UMET/DPMT 2011

Solution:

Such nucleophilic substitution reactions in which solvent acts as the nucleophile are called solvolysis reactions. Solvolysis of allylic halides occurs by $ S_N{1} $ mechanism due to greater stabilization of allyl carbocation intermediates by resonance. $1$-bromo-$3$-methylbut-$2$-ene react most rapidly by $ S_N1 $ mechanism.

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