Question

Predict the oxidation product of treating the given alkene with the reagent shown below. Include stereochemistry where applicable. Include H's on chirality centers. (mCPBA = mefa-chloroperoxybenzoic acid)

Answer 1

Concepts and reason

In synthetic organic chemistry, alkenes are unsaturated hydrocarbons with at least one carbon-carbon $\left( {{\rm{C}} = {\rm{C}}} \right)$ double bond present in a long chain. Alkenes are more reactive due to the presence of ${\rm{\pi }}$ -bonds. Alkenes undergo epoxidation reaction using peroxy acids.

Fundamentals

Epoxidation of alkenes:

Epoxides are cyclic ethers with three-membered rings. Alkenes, on reaction with peroxy acids, produce epoxides.

The structure of mCPBA is given below:

The mechanism for the epoxidation reaction is given below:

Ans:

The oxidation product, on treating the given alkene with a given reagent, is shown below:

Answer 2

Concepts and reason

This problem is based on the concept of stereochemistry of addition in alkene.

Since alkene has two electron clouds above and below the plane, the stereochemistry of addition either be syn- or anti.

Fundamentals

Alkene reacts with peroxybenzoic acid to give oxycyclopropanes (epoxides). This oxidation reaction is occurred in concerted manner, thus stereochemistry will be preserved in the product and addition is syn.

The structure of cyclohexene is as follows:

The structure of m-chloroperoxybenzoic acid (MCPBA) is as follows:

Ans:

The oxidation product is as follows:

Answer 3

Answer 4

mcpBA Meta-chloro per Ren Zeic aud → to epoxides 歹

Answer 5