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In nucleophilic substitution reactions, the feasibility of S_N1 or S_N2 mechanisms depends mainly on the nature of the carbon–halogen bond, the stability of the carbocation formed, and steric and electronic factors. (i) Benzyl chloride readily undergoes both S_N1 and S_N2 reactions. In the S_N1 mechanism, the C–Cl bond ionizes to form a benzyl carbocation, which is highly stabilized by resonance with the aromatic ring. This resonance stabilization lowers the energy barrier for carbocation formation, ___ _________ ____ ______ ___.
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