In the addition of hydrogen bromide to propene, consider which of the two possible products, 1-bromopropane and 2-bromopropane, will be the major product and why.

[Throughout the question, references will be made to a diagram which shows the mechanism of the reaction] In organic addition reactions like the one described in the question, an unstable intermediate carbocation forms after the electrophilic attack from the partially positive hydrogen on the hydrogen bromide. The alkyl groups in that carbocation are able to stabilise it a bit (so that it stays in that state until the bromide can make its nucleophilic attack) due to their positive induction effects: the alkyl groups push electron density towards the positive charge and away from themselves to lessen the density of that positive charge. When forming 1-bromopropane, the primary carbocation is stabilised by only one such positive induction effect. However, when forming 2-bromopropane, the secondary carbocation is stabilised by two positive induction effects, making it a more stable carbocation. Thus, the secondary carbocations are more likely to last longer for the bromide to complete its nucleophilic attack, leading to 2-bromopropane being the main product of the reaction.

AN
Answered by Aryan N. Chemistry tutor

15691 Views

See similar Chemistry IB tutors

Related Chemistry IB answers

All answers ▸

Explain the bonding in benzene, and hence its greater stability


How are Van der Waals interactions formed between molecules?


Explain why transition metals form coloured compounds when bonded to a ligand.


Is breaking bonds endothermic or exothermic?


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