See image — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

Concept: Sodium thiophenoxide (PhSNa) is a sulfur nucleophile. The sulfur anion (PhS⁻) acts as a nucleophile in an SN2 reaction with methyl bromide (CH3Br), which is a primary alkyl halide and an excellent substrate for SN2 substitution. Step 1: Identify the nucleophile and electrophile. PhSNa dissociates to give PhS⁻ (thiophenoxide anion) as the nucleophile and Na⁺ as the spectator ion. CH3Br is the electrophile. Step 2: Reaction mechanism. The sulfur atom of PhS⁻ attacks the electrophilic carbon of CH3Br in an SN2 fashion, displacing bromide ion (Br⁻). This forms Ph-S-CH3 (methyl phenyl sulfide, also called thioanisole) and NaBr as a byproduct. Step 3: Evaluate options. (a) Benzene - incorrect; no reduction or elimination is occurring under these conditions. (b) Bromobenzene - incorrect; no halogenation of the ring occurs here. (c) Ph-S-CH3 (thioanisole) - correct; direct SN2 alkylation of the thiophenoxide by methyl bromide. (d) Benzene - incorrect; same reasoning as (a). The solvent Et2O (diethyl ether) is a non-protic solvent that favors SN2 reactions and does not interfere with the nucleophile. Therefore, the correct answer is C.