Describe why phenol reacts more readily with bromine than benzene does.

(labelled diagrams of both benzene and phenol would be used to show the overlapping p orbitals above and below the plane of the molecule, with phenol showing the partial delocalisation of the oxygen lone pairs into the pi bond ring structure)Benzene is bonded covalently by a delocalised ring system of pi bonds. Each carbon is bonded to 3 other atoms (2 carbons and a hydrogen atom) by sigma bonds, leaving 1 electron delocalised in a p orbital. These p orbitals overlap sideways above and below the plane of the molecule and spread over all 6 carbons in the ring, forming a pi bond structure with low electron density (as the 6 delocalised electrons are spread over 6 carbons). This low electron density means that benzene cannot induce a dipole or attract electrophiles as easily as phenol.Phenol contains an oxygen atom which contributes a lone pair that partially delocalises into the pi bond structure, increasing its electron density. This means that its electrons can repel electrons in the Br-Br bond in bromine to induce a dipole, and can attract the positive charge on the electrophile more readily.

Answered by Abigail J. Chemistry tutor

7218 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Why does ice float on water? Use the structure of different states of matter to support your answer.


"A chromium compound contains 28.4% sodium and 32.1% chromium by mass, while the rest is oxygen. What is the empirical formula of this compound?"


Explain what the rate-determining step in a reaction is with reference to activation energy.


What is fractional distillation used for in industry? Explain the molecular basis behind it.


We're here to help

contact us iconContact usWhatsapp logoMessage us on Whatsapptelephone icon+44 (0) 203 773 6020
Facebook logoInstagram logoLinkedIn logo

© MyTutorWeb Ltd 2013–2025

Terms & Conditions|Privacy Policy
Cookie Preferences