An unknown alkene with molecular formula C7H12 undergoes the following reaction to give one product (below). What is the identity of the alkene?

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Correct Answer: C.
The reagents are indicative of the formation of an epoxide by mCPBA (m-chloroperoxybenzoic acid), followed by epoxide-opening using methylmagnesium bromide (Grignard reagent, a nucleophile). Epoxidation can occur from either side of the alkene (in this instance, epoxidation is shown from the top face). On treatment with the methyl Grignard reagent, backside attack occurs (in this instance, the nucleophile approaches from the back of the molecule), with nucleophilic addition to the least hindered epoxide carbon (steric effects).

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