In the nitration of toluene, which position is most likely to be attacked by the electrophile?
Practice Questions
1 question
Q1
In the nitration of toluene, which position is most likely to be attacked by the electrophile?
Ortho position
Meta position
Para position
All positions equally
The para position is favored in the nitration of toluene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Questions & Step-by-step Solutions
1 item
Q
Q: In the nitration of toluene, which position is most likely to be attacked by the electrophile?
Solution: The para position is favored in the nitration of toluene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Steps: 6
Step 1: Understand that toluene is a benzene ring with a methyl group (CH3) attached to it.
Step 2: Recognize that the methyl group is an electron-donating group, which means it helps to increase the electron density on the benzene ring.
Step 3: Identify the positions on the benzene ring where the electrophile can attack: the ortho position (next to the methyl group), the meta position (one carbon away from the methyl group), and the para position (opposite the methyl group).
Step 4: Realize that the electron-donating effect of the methyl group stabilizes the carbocation intermediate that forms when the electrophile attacks the ring.
Step 5: Determine that the para position is more stable than the ortho position because steric hindrance (crowding) is less at the para position.
Step 6: Conclude that the para position is favored for electrophilic attack during the nitration of toluene.
