Reaction of C₆H₅CH₂Br with aqueous sodium hydroxide follows

(i) S_N¹ mechanism

(ii) S_N² mechanism

(iii) Any of the above two depending upon the temperature of reaction

(iv) Saytzeff rule

<p><span data-teams="true">This is a multiple choice answer as classified in NCERT Exemplar</span></p><p>The Correct Answer is Option (i).</p><p>When benzyl chloride is treated with aqueous sodium hydroxide, where <strong>-OH</strong> is the nucleophile, a nucleophilic substitution reaction occurs, resulting in the formation of benzyl alcohol. The benzene ring is resonance stabilised here, and this stability is extended to the connected methylene group, giving a positive charge to <strong>-CH₂</strong>, making the whole carbocation stable when the link between benzyl and bromide is broken. This is an <strong>S_N¹</strong> reaction with two stages that is followed due to the stability of the carbocation. This is a coordinated reaction that takes place in two phases. The halide group first exits the carbocation, and then the nucleophile binds to the cation, producing alcohol. The right answer is (i).</p>

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