Q20-E - Organic Chemistry (Mcmurry)

Question

Show the product, including stereochemistry, that would result from reaction of the following epoxide with HBr

Step-by-Step Solution

Answer

Step 1: Reaction of epoxide with alkyl halide

When epoxide reacts with the alkyl halide opening of the chain occur and act as electrophilic which lead to formation of hydroxy group and them followed by \(S{N_2}\) mechanism and addition of halide occur.

Step 2: Reaction of given epoxide with HBr

On reaction with the alkyl halide ring opening occur at the tertiary carbon and give carbocation like stability and hydroxy group formation occurs and bromine attack occur form the 180° as it follow \(S{N_2}\) mechanism and the stereo remain the same as shown below:

                                                Ring opening of epoxide