Which of the following compounds undergoes electrophilic substitution more readily?
Practice Questions
1 question
Q1
Which of the following compounds undergoes electrophilic substitution more readily?
Toluene
Benzene
Chlorobenzene
Nitrobenzene
Toluene undergoes electrophilic substitution more readily than benzene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Questions & Step-by-step Solutions
1 item
Q
Q: Which of the following compounds undergoes electrophilic substitution more readily?
Solution: Toluene undergoes electrophilic substitution more readily than benzene due to the electron-donating effect of the methyl group, which stabilizes the carbocation intermediate.
Steps: 7
Step 1: Understand what electrophilic substitution is. It is a reaction where an electrophile replaces a hydrogen atom in an aromatic compound.
Step 2: Identify the compounds in the question. We are comparing toluene and benzene.
Step 3: Know the structure of toluene. Toluene has a methyl group (CH3) attached to a benzene ring.
Step 4: Understand the role of the methyl group. The methyl group is an electron-donating group, which means it can push electrons towards the benzene ring.
Step 5: Recognize the effect of electron donation. The electron-donating effect of the methyl group stabilizes the positive charge (carbocation) that forms during the electrophilic substitution reaction.
Step 6: Compare the stability of the carbocation intermediates. Toluene's carbocation is more stable than benzene's because of the methyl group's electron-donating effect.
Step 7: Conclude that since toluene's carbocation is more stable, toluene undergoes electrophilic substitution more readily than benzene.
