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

14814 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Why is scandium not considered a true transition metal?


An iron-alloy nail (2.41g) is dissolved in 100cm3 acid. 10cm3 portions of this solution are titrated with KMnO4 (0.02M) and 9.80cm3 of KMnO4 was needed to react with iron solution. What % of iron by mass is in the nail?


0.28 g of a gaseous hydrocarbon was turned in excess oxygen. 0.88 g of carbon dioxide and 0.36 g of water were formed. The volume of 0.28 g of the hydrocarbon at 1.01 x10^5 Pa and 298 k is 123 cm^3. Work out the molecular formula of the hydrocarbon.


Explain why the product of a nucleophilic addition to butanone does not effect plane polarized light.


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