Which of the following is most reactive towards $\mathrm{S}_{\mathrm{N}} 2$ reaction?
Which of the following is most reactive towards $\mathrm{S}_{\mathrm{N}} 2$ reaction?
Solution
4-nitrobenzyl chloride is likely to react by the $\mathrm{S}_{\mathrm{N}} 2$ mechanism as the strongly electronwithdrawing nitro group would destabilize the carbocation intermediate of the $\mathrm{S}_{\mathrm{N}} 1$ mechanism, a benzylic chloride that disfavours the $\mathrm{S}_{\mathrm{N}} 1$ mechanism.
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