Question

What product is obtained when you epoxidize (d)-(+)-carvone with mcpba? Why do you obtain this product?

What product is obtained when you epoxidize (d)-(+)-carvone with mcpba? Why do you obtain this product?

Homework Answers

Answer #1

Epoxidation with mCPBA adds an oxygen to the double bond in a syn fashion by a concerted manner to form an epoxide. The structure of d-(+)-carvone epoxide product formed here would be as shown here.

The product is obtained by addition of oxygen from the mCPBA coming from the opposite side of the already existing methyl group. This will exert least steric hindrance and hence is formed as the product of the reaction.

Figure showing the structure of d-(+)-carvone oxide

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