Q21E - Organic Chemistry (Mcmurry)

Question

Show the product, including stereochemistry, of the following reaction:

Step-by-Step Solution

Answer

A reaction followed as:

Step 1: Reaction of epoxide with Grignard reagent

When the reaction of an epoxide occurs with the Grignard reagent opening of the epoxide occurs that the breaking of the C-O bond occurs and then oxygen act as electrophilic which leads to the formation of the hydroxy group followed by mechanism.

Step 2: Reaction of given epoxide with CH 3 MgBr

The reaction of epoxide with the methyl magnesium bromide opening occurs at the secondary carbon because Grignard reagent attack from the less hindered side and hydroxy group formation occurs followed by the SN₂ mechanism and the stereo remain same without any change as shown below: