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

14807 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

What is the evidence that disproves the Kekule model for benzene?


What affects the boiling point of an alkane and why?


Why is benzene more stable than expected?


A solution of acetic acid and sodium acetate was prepared, by dissolving 4.1 g of sodium acetate in 750 cm^3 of 0.085 mol/dm^3 acetic acid, at 25 degrees. 10 Cm^3 of 2 mol/dm^3 HCl was added. Ka is 1.76*10^-5, calculate and explain the change in pH


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