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.

Answered by Miles P. Chemistry tutor

1824 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Why is the melting point of saturated carbon chains greater than unsaturated carbon chains?


Q2. Calculate the pH of the solution formed after 50.0 cm^3 of 0.0108 mol/dm^3 aqueous sodium hydroxide are added to beaker B. Give your answer to 2 decimal places


Why does the ionisation energy of period 2 elements increase along the period, but drop for boron and oxygen?


What is the difference between London dispersion forces and hydrogen bonds?


We're here to help

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