Question

Secondary butyl chloride undergo alkaline hydrolysis in the polar protic solvent by ______ mechanism.

• A. $S_{N}2$
• B. $S_{N}1$
• C. $S_{N}1$ and $S_{N}2$
• D. None of the above

Answer 1

The correct option is B $S_{N}1$

In polar protic medium secondary alkyl halide undergo $S_{N}1$ mechanism.

Polar protic solvents solvate the nucleophile and make then less nucleophilic which favours $S_{N}1$ over $S_{N}2$ reaction mechanism.

The carbocation intermediate formed during the $S_{N}1$ mechanism is very stable in polar protic solvents.