JEE Main Chemistry question

A methyl ketone bearing a pendant –CH₂CH₂COOH chain --K₂Cr₂O₇/H⁺--> B + C. Here B and C are

(A)CH₃COCH₂COOH and CH₃COOH (oxidative cleavage products)Correct
(B)HOOC–CH₂–COOH and HOOC–CH₃ variants
(C)CH₃COOH and HO–C(CH₃)₂–COOH
(D)None of the above

Answer: (A)

Solution

Vigorous oxidation (acidic dichromate) of a methyl ketone bearing an extended chain can oxidatively cleave at the position adjacent to the carbonyl via enolization, breaking the carbon skeleton into two carbonyl-bearing fragments: a shorter keto-acid fragment (retaining the original ketone and the existing

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Question ID VK-149442