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.

Answered by Nketia O. Chemistry tutor

11775 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

Why does an ionic compound (e.g. NaCl) conduct electricity when molten or dissolved in water, but not when it is a solid.


(i) What property does Magnesium Oxide have that makes it useful to create heat-resistant bricks to line furnaces? (ii) Explain why H2S exists as a gas and H2O exists as a liquid (at r.t.p).


What is enthalpy and how can it be calculated?


How does a heterogenous catalyst work? (3 marks)


We're here to help

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

© MyTutorWeb Ltd 2013–2024

Terms & Conditions|Privacy Policy
Cookie Preferences