Join thousands of students who trust us to help them ace their exams!Watch the first video
Multiple Choice
Which of the following reactions is responsible for the inversion of stereochemistry in a nucleophilic substitution reaction?
A
SN2 reaction
B
E2 reaction
C
E1 reaction
D
SN1 reaction
Verified step by step guidance
1
Understand the concept of stereochemistry inversion: In organic chemistry, stereochemistry refers to the spatial arrangement of atoms in molecules. Inversion of stereochemistry means that the configuration of the molecule changes, often flipping from one enantiomer to another.
Identify the type of nucleophilic substitution reactions: There are two main types of nucleophilic substitution reactions, SN1 and SN2. SN1 involves a two-step mechanism with a carbocation intermediate, while SN2 involves a one-step mechanism where the nucleophile attacks the substrate directly.
Examine the SN2 reaction mechanism: In an SN2 reaction, the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, leading to a backside attack. This results in the inversion of configuration at the carbon center, often described as a 'Walden inversion'.
Compare SN2 with other reactions: SN1 reactions do not lead to stereochemistry inversion because they involve a planar carbocation intermediate, allowing the nucleophile to attack from either side, often resulting in a racemic mixture. E1 and E2 are elimination reactions and do not involve nucleophilic substitution.
Conclude why SN2 is responsible for inversion: The direct backside attack in SN2 reactions is the key reason for the inversion of stereochemistry, distinguishing it from SN1, E1, and E2 reactions.