JEE Main Chemistry question

ChemistryHaloalkanes and HaloarenesJEE Main

Cyclohexene oxide (the epoxide of cyclohexene, i.e. a cyclohexane ring with an oxygen bridging two adjacent ring carbons) is treated with in dry ether, followed by aqueous acidic work-up. How many carbon atoms are present in the major organic product?

Answer: 7

Solution

Methylmagnesium bromide opens the strained epoxide ring via attack at one of the two ring carbons bearing the epoxide oxygen, installing a methyl group there and generating an alkoxide at the adjacent ring carbon, which is protonated on acidic work-up to give

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Question ID VK-148990