How does electrophilic aromatic substitution occur?

The delocalised ring in aromatic compounds (such as benzene) is very stable and therefore requires a very strong electrophile to be created before it will react. An example of this would be the formation of the nitronium ion (NO2+) from sulfuric acid and nitric acid, where the nitric acid acts as a base by accepting a proton in the following reaction:H2SO4 + HNO3 -> HSO4- + NO2+ + H2OUsing the whiteboard I can then outline the mechanism for this reaction, showing how the nitronium ion breaks the aromatic delocalised ring, then the ring reforms by eliminating a hydrogen atom. This hydrogen atom then goes on to react with the hydrogen sulfate HSO4- ion to reform sulfuric acid, thus making sulfuric acid a catalyst in this reaction.We can draw parallels with this reaction to many other electrophilic substitution reactions such as chlorination, bromination and Friedel-Crafts alkylation reactions as they are all very similar in principle.

MP
Answered by Miles P. Chemistry tutor

2205 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Calculate the pH of the solution formed when 30 cm3 of 0.150 moldm-3 aqueous sulfuric acid is added to 30 cm3 of 0.200 moldm-3 aqueous potassium hydroxide at 25 C.


The Haber process is used to produce ammonia. (Insert equation here) Explain the optimum conditions for this reaction and why these may differ from the conditions used in industry.


State and explain the general trend in the first ionisation energy across a period.


Explain the trend in boiling points between HF, HCl and HBr.


We're here to help

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

© MyTutorWeb Ltd 2013–2025

Terms & Conditions|Privacy Policy
Cookie Preferences