Benzyl iodide can either react via S_N2 or S_N1 substitution mechanism. Since Benzyl iodide is a 1* alkyl halide it is expected to react via S_N2 and not S_N1.

Draw the mechanism for the S_N1 substitution reaction and determine how this primary halide undergoes S_N1 reactions.

• A. Benzyl chloride can undergo S_N1 reaction because primary halides prefer S_N1
• B. Benzyl chloride can undergo S_N1 reaction due to strong nucleophile.
• C. Benzyl chloride can undergo S_N1 presence of aromatic ring.
• D. Benzyl chloride can undergo S_N1 reaction due to resonance stabilization of intermediate carbocation.

Answer: (D)