Why is there a difference in mechanism between tertiary halogenoalkanes and primary halogenoalkanes in nucleophilic substitution?

The difference in mechanism between tertiary halogenoalkanes and primary halogenoalkanes is caused by the difference in relative stability between the two carbocation intermediates formed. In the case of tertiary halogenoalkanes which have methyl groups attached to the functional group carbon, the methyl groups are able to stabilise the positive charged formed upon nucleophilic attack on the functional group carbon, making the intermediate more stable. This is not seen in primary halogenoalkanes, where the inductive stabilising effect of the functional group carbon is only caused by one methyl group as opposed to three. This is why tertiary halogenoalkanes follow Sn1, and primary halogenoalkanes follow Sn2.

NO
Answered by Nketia O. Chemistry tutor

14806 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Give the IUPAC name of CH3CH2CH2CH2CH(OH)CN and describe why the formation of this molecule creates 2 enantiomers.


How do ionic charge and radius affect lattice enthalpy?


What is the difference between empirical and molecular formula?


Would you expect a calcium ion to be bigger, smaller or the same size as a calcium atom? Give TWO reasons to explain your answer.


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:

© 2026 by IXL Learning