Question

Reaction of $C_6{H}_{5}C{H}_{2}Br$ with aqueous sodium hydroxide follows_____

• A. $S_{N}1$ mechanism
• B. $S_{N}2$ mechanism
• C. Any of the above two depending upon the temperature of reaction
• D. Saytzeff's rule

Answer 1

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

In the given reaction, the solvent is aq. NaOH which is polar protic and thus the reaction will proceed through $S_{N}1$ mechanism. Also the intermediate formed is $C_6{H}_{5}C{H}_2^{+}$ which is more stable carbocation because of resonance. As we know the stability of carbocation is directly proportional to the $S_{N}1$ mechanism. Hence, the reaction will follow $S_{N}1$ mechanism out of the given four options.