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Chapter 12: PROBLEM 12.47 (page 490)

Question: Draw the products formed after Steps and in the following three-step sequence. Then draw stepwise mechanisms for each step.

Short Answer

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Answer

Step by step solution

01

m-CPBA

m-CPBA is represented by the name meta-chloroperbenzoic acid, which is used for the formation of an epoxide at the double bond.

02

Conversion of epoxide into ether

When undergoing ring-opening, epoxides give alcohol that forms ether by attacking the C-X bond, where X is the halogen (Cl, Br, or I).

03

Explanation

The given substrate is an alkene with a halide bond. m-CPBA forms an epoxide at the alkene by giving oxygen to the alkene.

The base HO-attacks the epoxide from the less substituted site and forms diol.

In the third step, the base NaH abstracts the acidic hydrogen of OH, which leads to the attack of oxide on the C-Br bond.

The mechanism is shown as:

Ring opening of the epoxide

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