Question

An SN2 reaction is a substitution reaction in which a nucleophile attacks an electrophile and displaces a leaving group in one step. If the electrophile is a chiral center, what happens to its stereochemistry?

Answer 1

In an SN2 reaction at a chiral center, the stereochemistry inverts due to the nucleophile attacking from the opposite direction of the leaving group.

Step-by-step explanation:

SN2 reactions involve a nucleophile attacking an electrophile and displacing a leaving group in a single, concerted step. If the electrophile is a chiral center, an inversion of stereochemistry occurs during the reaction. This happens because the incoming nucleophile approaches the electrophilic carbon from the side opposite to the leaving group, leading to a 'backside attack'. As this substitution occurs, the other groups attached to the chiral center shift to the opposite side, resulting in the inversion of configuration. This step is bimolecular, as both the nucleophile and the substrate are involved in the rate-determining step of the reaction.

In an SN2 reaction, if the electrophile is a chiral center, its stereochemistry will be inverted. This is because the incoming nucleophile attacks the electrophile from the side opposite to the leaving group, leading to inversion of stereochemistry. This mechanism is called S2, where S stands for substitution, N for nucleophilic, and 2 for bimolecular.