What is the stereochemical outcome of the electrophilic substitution of 1,2-dimethylbenzene (o-xylene) at the 5-position?
Practice Questions
1 question
Q1
What is the stereochemical outcome of the electrophilic substitution of 1,2-dimethylbenzene (o-xylene) at the 5-position?
Only one product
Two diastereomers
A racemic mixture
No reaction
Electrophilic substitution at the 5-position of o-xylene leads to two diastereomers due to the presence of two chiral centers.
Questions & Step-by-step Solutions
1 item
Q
Q: What is the stereochemical outcome of the electrophilic substitution of 1,2-dimethylbenzene (o-xylene) at the 5-position?
Solution: Electrophilic substitution at the 5-position of o-xylene leads to two diastereomers due to the presence of two chiral centers.
Steps: 5
Step 1: Understand that 1,2-dimethylbenzene (o-xylene) has two methyl groups attached to the benzene ring at the 1 and 2 positions.
Step 2: Identify the 5-position on the benzene ring, which is opposite to the 1 and 2 positions.
Step 3: Recognize that electrophilic substitution involves replacing a hydrogen atom on the benzene ring with an electrophile at the 5-position.
Step 4: Note that when the electrophile substitutes at the 5-position, it creates two new chiral centers because the two methyl groups at the 1 and 2 positions can create different spatial arrangements.
Step 5: Understand that these different arrangements lead to two distinct diastereomers, which are stereoisomers that are not mirror images of each other.
