JEE Main Chemistry question

with and substituents, i.e. Ph-C(CH_3)(OH)-C(CH_3)(OH)-Ph (a pinacol), in the reaction Ph–C(CH₃)(OH)–C(CH₃)(OH)–Ph . The product is

(A)The pinacolone-type rearranged ketone, Ph-C(CH_3)_2-CO-PhCorrect
(B)Ph-CH(CH3)-CO-CH3-Ph type unrearranged product
(C)A diene from simple dehydration
(D)None of the above

Answer: (A)

Solution

This symmetric 1,2-diol (a "pinacol" analogue) undergoes the pinacol–pinacolone rearrangement under conc. : protonation and loss of water gives a benzylic carbocation, and a 1,2-phenyl (or methyl) shift from the adjacent carbon

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Question ID VK-148568