Question

Which one of the following alkyl bromide undergoes
most rapid solvolysis in methanol solution to give
corresponding methyl ether?​

Answer 1

Option 1 (1-bromo-3-methylbut-2-ene) will go most rapid solvolysis in methanol solution to give  corresponding methyl ether.

• The nucleophilic substitution reaction where solvent acts as the nucleophile are called solvolysis reactions.

• Solvolysis of allylic halides occurs by the mechanism called SN1 , due to   resonance and greater stabilization of allyl carbocation intermediate in the ionic structure.

Therefore 1-bromo-3-methylbut-2-ene will go most rapid solvolysis in methanol solution to give  corresponding methyl ether by SN1 mechanism.