Question

The compound which can show $S_{N}2$ reaction during solvolysis is:

• A.
• B.
• C.
• D.

Answer 1

The correct option is B

For solvolysis, the solvent has to break the bond between the leaving group and the carbon to which the leaving group is attached. And it is given that the proposed pathway or mechanism is via $S_{N}2$. In an $S_{N}2$, hydroxide is a very poor leaving group. In aniline and chlorobenzene, the substituent on the benzene ring are attached to a relatively more electronegative $s{p}^2$ hybrid carbon. So between 1-phenylethanol and 1-phenylethylchloride, the latter is more suited for an $S_{N}2$ solvolysis.