Q27 of 37 Page 1

Which one of the following compounds will undergo hydrolysis at a faster rate by SN1 mechanism? Justify.


Allylic and benzylic halides show higher reactivity towards SN1 mechanism for hydrolysis, hence the benzyl chloride will undergo hydrolysis at a faster rate. The SN1 mechanism is a two-step process where the first step is the formation of carbocation after the cleavage of the C-X bond, and the second step is the attack by a nucleophile to complete the reaction. The order of reactivity is tertiary halides > secondary halides > primary halides. This is because the tertiary carbocation formed is highly stable. The benzyl carbocation is more stable due to resonance stabilization. The resonating structure is as follows:


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