Which of the following syntheses will best produce the following target molecule?

• A.
• B.
• C.
• D.

Answer: (A)

Verified step by step guidance

1. Identify the target molecule as an epoxide, which is a three-membered cyclic ether.
2. Recognize that the starting material is an alkene, which can be converted into an epoxide using an oxidizing agent like mCPBA (meta-chloroperoxybenzoic acid).
3. Consider the first step in the synthesis: the addition of HBr in the presence of H2O2, which suggests an anti-Markovnikov addition to form a bromoalkane.
4. The next step involves the use of NaNH2, which can dehydrohalogenate the bromoalkane to form an alkyne.
5. The alkyne is then partially hydrogenated using Lindlar's catalyst to form a cis-alkene, which can be epoxidized using mCPBA to form the desired epoxide.