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Chapter 17: Q27E (page 567)

Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

Short Answer

Expert verified

The mechanism followed as:

Step by step solution

01

Reaction of epoxide with Grignard reagent

Epoxide on reaction with Grignard reagent opens as an electrophile on the addition of the alkyl group of the Grignard reagent, and the formation of alcohol occurs.

The hydroxyl group and the alkyl group of the Grignard reagent have trans relations with each other.

02

Reaction of given epoxide with Grignard reagent

The given epoxide reacts with the methyl magnesium bromide to form the intermediate called alkoxide because oxygen has a negative charge, followed by hydrolysis so that the negatively charged oxygen gains the proton, and hydroxyl formation occurs.

03

Mechanism

  1. React with methyl magnesium bromide

  2. Alkoxide formation

  3. Hydrolysis

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TMS ethers can be removed by treatment with fluoride ion as well as by acid-catalyzed hydrolysis. Propose a mechanism for the reaction of cyclohexyl TMS ether with LiF. Fluorotrimethylsilane is a product.

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b)

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