JEE Main Chemistry question

Which of the following alkenes will yield 2-butanone on ozonolysis followed by the reaction with Zn/HO? [AMU 2004]

(A)2-methyl-2-hexene
(B)2-methyl-1-hexene
(C)3,4-dimethyl-3-hexeneCorrect
(D)2,3-dimethyl-3-hexene

Answer: (C)

Solution

2-Butanone (CHCOCH) requires an alkene carbon bearing exactly one methyl and one ethyl substituent, i.e. (CH)(CH)C=. In 3,4-dimethylhex-3-ene, CHCH–C(CH)=C(CH)–CHCH, both alkene carbons carry a methyl branch plus an ethyl

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Question ID VK-142154