Q. 235.0( 2 Votes )

Reaction of C6H5CH2Br with aqueous sodium hydroxide follows ____________.
A. SN1 mechanism
B. SN2 mechanism
C. Any of the above two depending upon the temperature of reaction
D. Saytzeff rule

Answer :

When benzyl chloride is treated with aqueous sodium hydroxide, where OH is the nucleophile, nucleophilic substitution reaction takes place forming benzyl alcohol. Here, the benzene ring is resonance stabilized and its stability is extended to the methylene group attached, giving a positive charge to –CH2, making the whole carbocation stable when the bond between benzyl and bromide is broken.

This reaction is SN1 reaction, it has two steps, and is followed due to the stability of carbocation. This reaction is concerted and occurs in two steps. First, the halide group leaves the carbocation, and the nucleophile then attaches itself to the cation, forming alcohol. The correct option is (i).

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