Alcohols and carbonyls differ in their reactivity towards phosphorus pentachloride
Alcohols and carbonyls react differently with phosphorus pentachloride: alcohols are converted into alkyl chlorides, whereas ketones and other carbonyl compounds yield alkenyl chlorides or undergo chlorination via distinct pathways.
The retrieved literature documents specific, distinct reaction pathways for alcohols (reacting to form alkyl chlorides) and carbonyl compounds like ketones (reacting to yield alkenyl chlorides) when treated with phosphorus pentachloride, confirming that they differ in their reactivity.
RM Carman, IM Shaw. The reaction of tertiary alcohols with phosphorus pentachloride. 1976. https://doi.org/10.1071/ch9760133
Paper 0 establishes that phosphorus pentachloride reacts with tertiary alcohols to produce tertiary chlorides.
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Müller DS. Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review.. 2026. https://doi.org/10.3762/bjoc.22.1
Paper 8 notes that phosphorus pentachloride reacts with ketones (carbonyls) to yield alkenyl chlorides.
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