What is the correct stereochemistry of the product of the following reaction:

Question

Quizplus · Accepted Answer

The reaction involves a cyclic intermediate where the OH and Br are anti to each other in the chair conformation. The OH group attacks from the same face as the axial Br, leading to retention of configuration at the stereocenter. Therefore, the product will have the same configuration as the starting material at the stereocenter on C2, which is R. The Br group is equatorial in the starting material, so it will be axial in the product. The stereochemistry at C3 will be inverted due to the chair flip that occurs during the cyclization step, giving the product a configuration of 2R,3S.

What Is the Correct Stereochemistry of the Product of the Following