Explain the resistance to bromination of benzene in comparison to phenol.

In phenol, one of the lone pairs of electrons in a p-orbital of the oxygen atom in the -OH group overlaps with the delocalised ring of electrons in the ring. This lone pair is partially delocalised into the pi-system in the benzene ring. This increases electron density of the ring, meaning it is able to induce a dipole in Br2 and so can undergo electrophilic substitution. In benzene, the electrons are delocalised which means the negative charge is spread out through the ring causing benzene to have a lower electron density and so can't induce a dipole in Br2.

CH
Answered by Cerys H. Chemistry tutor

3592 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Explain the trend of first ionisation energy down a group.


How do you answer a long answer question on how buffer systems work?


A student reacts 50.0cm^3 of 2.00mol dm^-3 HCl with 25.0cm^3 NaOH. What is the concentration of NaOH?


What is the meaning of the term 'structural isomers'?


We're here to help

contact us iconContact ustelephone icon+44 (0) 203 773 6020
Facebook logoInstagram logoLinkedIn logo

MyTutor is part of the IXL family of brands:

© 2025 by IXL Learning