What is the mechanism and major product when benzyl chloride reacts with water under acidic conditions?

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Multiple Choice

What is the mechanism and major product when benzyl chloride reacts with water under acidic conditions?

The key idea is that benzylic halides favor SN1 in acidic aqueous environments because the benzylic carbocation formed after the leaving group departs is highly stabilized by resonance with the phenyl ring. In this reaction, chloride leaves first to give that resonance-stabilized carbocation. Water then attacks the carbocation, forming protonated benzyl alcohol, which loses a proton to give benzyl alcohol. So the mechanism is SN1 and the major product is benzyl alcohol. An SN2 pathway would be disfavored here since the medium is strongly acidic and water is a weak nucleophile, and forming benzaldehyde would require oxidation, not hydrolysis.

The key idea is that benzylic halides favor SN1 in acidic aqueous environments because the benzylic carbocation formed after the leaving group departs is highly stabilized by resonance with the phenyl ring. In this reaction, chloride leaves first to give that resonance-stabilized carbocation. Water then attacks the carbocation, forming protonated benzyl alcohol, which loses a proton to give benzyl alcohol. So the mechanism is SN1 and the major product is benzyl alcohol. An SN2 pathway would be disfavored here since the medium is strongly acidic and water is a weak nucleophile, and forming benzaldehyde would require oxidation, not hydrolysis.

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