Why is phenylamine a weaker organic base than ethylamine?

Phenylamine contains a phenyl group attached to the amine. Phenyl groups have a delocalised system of electrons as a result of p orbitals from the 6 adjacent carbon atoms overlapping and "merging" together to form a 9very stable) delocalised pi bond with 6 electrons. The lone pair of the nitrogen atom in the amine group is "drawn in" towards this delocalisation and this interaction makes the lone pair less available to bond to an incoming H+ ion. In comparison, ethylamine has no delocalisation in the molecule. In fact, there is actually a positive inductive effect contributed from the alkyl groups of the ethylamine which pushes the lone pair away from the N atom and makes the lone pair more available to bond to an H+ ion. The availability of a lone pair of electrons on a base determines its strength as it is these electrons that will "mop up" H+ ions in solution and hence increase pH towards more alkaline conditions. Therefore, phenylamine is a weaker base than ethylamine because its lone pair is less available.

AW
Answered by Adam W. Chemistry tutor

34046 Views

See similar Chemistry A Level tutors

Related Chemistry A Level answers

All answers ▸

A sample of CaCO3 has been weighed in at 6.3 g. How many moles of calcium carbonate are present?


Describe the products of the following Friedl-Crafts substitution and explain the role of the AlCl3 in the reaction: C6H6 + CH3C(O)Cl + AlCl3 = ?


Describe how to perform a flame test to identify an unknown compound.


Explain why potassium has a greater first ionisation energy than rubidium.


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