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Among the given options, only PCl5 can convert an alcoholic group as well as a carboxyl group to chloride. The correct option is:

1. RCH2OH → PCl5 → RCH2Cl
2. RCOOH → PCl5 → RCOCl
3. RCH2OH → SOCl2 → RCH2Cl
4. RCOOH → SOCl2 → RCOCl

Correct answer: RCOOH → PCl5 → RCOCl

Solution

PCl5 can convert both alcohols to alkyl chlorides and carboxylic acids to acyl chlorides. Option B specifically shows the conversion of a carboxylic acid to an acyl chloride using PCl5.

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