What is the mechanism for the nucleophilic substitution of a halogenoalkane?

A halogenoalkane is a saturated hydrocarbon chain with a halogen atom (F, Cl, Br or I) attached to a carbon instead of a hydrogen. Halogens have a greater electronegativity than carbon. This means they draw the shared electron pair towards them, which polarises the carbon-halogen bond, and gives the carbon a slight delta positive charge. A nucleophile is a species with a lone pair of electrons. It is attracted to the slightly positive carbon, and donates its lone pair of elections to the carbon to form a bond. This pushes the electrons from the C-halogen bond to the halogen (remember carbon can only have 8 electrons in its valence shell), so that the halogen leaves the carbon compound as a negative halide ion. 

CS
Answered by Charlotte S. Chemistry tutor

4021 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

What factors affect ionisation energy and how does each of them affect it?


What's the difference between an electrophile and a nucleophile?


Explain what is meant by the term 'rate of reaction'?


But-1-ene reacts with HBr to form a saturated compound, name and draw the mechanism, then explain how three isomeric products are formed.


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