The ketone shown is treated with m-CPBA; the product is heated with aqueous $NaOH$ , and the resulting organic compound is finally oxidised with excess Jones reagent. Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The compound is phenylacetone (1-phenylpropan-2-one). Benzyl migrates in preference to methyl, so Baeyer-Villiger gives benzyl acetate. Alkaline hydrolysis releases benzyl alcohol and acetate, and Jones reagent oxidises the primary benzylic alcohol to benzoic acid. Methyl migration would have given methyl phenylacetate and then phenylacetic acid.

Practice Reduction, Oxidation and Hydrolysis in Organic Chemistry More on HIO4 cleavage and Baeyer-Villiger of drawn compounds

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The ketone shown is treated with m-CPBA; the product is heated with aqueous NaOH, and the resulting organic compound is finally oxidised with excess Jones reagent. Which structure is the final product?

Answer: B

More questions on HIO4 cleavage and Baeyer-Villiger of drawn compounds

The ketone shown is treated with m-CPBA; the product is heated with aqueous $NaOH$ , and the resulting organic compound is finally oxidised with excess Jones reagent. Which structure is the final product?