Chemistry · Common types of organic reactions: Substitution, addition, elimination and rearrangement
Which one of the following undergoes nucleophilic substitution exclusively by me
Which one of the following undergoes nucleophilic substitution exclusively by \( \boldsymbol{S}_{N} 1 \) mechanism?
- A. Benzyl chloride
- B. Ethyl chloride
- C. chlorobenzene
- D. Isopropyl chloride
Step-by-step solution
Benzyl chloride can form a resonance-stabilized benzyl carbocation, making SN1 mechanism highly favorable. Primary alkyl halides (ethyl chloride) undergo SN2, aryl halides (chlorobenzene) are inert to both under normal conditions, and secondary alkyl halides (isopropyl chloride) can undergo both SN1 and SN2, not exclusively SN1. Thus, benzyl chloride is the only one that undergoes nucleophilic substitution predominantly via SN1.
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