See image — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

Concept: SN2 reactions require a good nucleophile attacking a substrate at a carbon bearing a leaving group (halide), proceeding with inversion of configuration. The substrate must be accessible (primary or secondary alkyl halides work well; tertiary alkyl halides do not undergo SN2 due to steric hindrance). Option (a): Cyclohexylmethanol (cyclohexane-CH2OH) can be synthesized by SN2 displacement of cyclohexylmethyl halide (a primary alkyl halide, -CH2X) using hydroxide (OH-) as the nucleophile. Primary alkyl halides are excellent SN2 substrates. This works. Option (b): Cyclohexyl ethyl sulfide (cyclohexane-SCH2CH3) can be synthesized by SN2 displacement. Two routes are possible: (i) cyclohexyl halide (secondary) attacked by ethanethiolate (CH3CH2S-), a very good nucleophile (sulfur nucleophiles are excellent in SN2 due to high polarizability), or (ii) ethyl halide (primary) attacked by cyclohexanethiolate. Secondary alkyl halides can undergo SN2 with strong, polarizable nucleophiles like thiolates. This works. Option (c): Me3C-OCH3 (tert-butyl methyl ether) - if attempted via SN2, the substrate would need to be tert-butyl halide (tertiary), which cannot undergo SN2 due to severe steric hindrance at the neopentyl-like tertiary carbon. However, it could be synthesized by SN2 on methyl halide (CH3X) using tert-butoxide as nucleophile, or methanol attacking methyl halide - wait, more precisely: tert-butoxide (nucleophile) + CH3X (primary methyl halide, excellent SN2 substrate) → Me3C-OCH3. Methyl halides are the least hindered substrates and undergo SN2 very readily. This works. Since all three compounds (a), (b), and (c) can be synthesized via an SN2 displacement of an alkyl halide, the answer is (d) All of these. Therefore, the correct answer is D.