Question

t-Butyl chloride preferably undergoes hydrolysis by:

• A. $S_{N}1$ mechanism
• B. $S_{N}2$ mechanism
• C. Any of (a) and (b)
• D. None of the above

Answer 1

The correct option is A $S_{N}1$ mechanism

The $S_{N}1$ reaction proceeds stepwise. The leaving group first leaves, where upon a carbocation forms that is attacked by the nucleophile.

The $S_{N}2$ occurs in one step. Both the nucleophile and substrate are involved in the rate determining step. Therefore, the rate is dependent on both the concentration of substrate and that of the nucleophile.

For tertiary butyl chloride, it forms tertiary carbocatin which is highly stable, So tertiary butyl chloride undergoes hydrolysis by $S_{N}1$ mechanism. Hence, the correct option is (a).