Reaction of $C_{6} H_{5} C H_{2} B r$ 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 rule

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Solution

Answer: (a). $S_{N} 1$ mechanism depends upon the stability of carbocation. Higher the stability of carbocation, higher will be the possibility of $S_{N} 1$ mechanism to take place. In the given compound, $C_{6} H_{5} C H_{2} B r$ carbocation is $C_{6} H_{5} \oplus C H_{2}$ . This carbocation $C_{6} H_{5} \oplus C H_{2}$ is a stable carbocation due to resonance, therefore its show $S_{N} 1$ mechanism.

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