Base Properties (Oxford AQA International A Level Chemistry)

Revision Note

Philippa Platt

Written by: Philippa Platt

Reviewed by: Stewart Hird

Base Properties of Amines

  • The nitrogen atom in ammonia and amine molecules can accept proton (H+ ion)

  • They can therefore act as bases in aqueous solutions by donating its lone pair of electrons to a proton and form a dative bond

    • For example, ammonia undergoes an acid-base reaction with dilute hydrochloric acid (HCl) to form a salt

NH3 + HCl → NH4+Cl-

base      acid            salt

  • Amines react with HCl to form amine salts, such as ethylammonium chloride

C2H5NH2 + HCl → C2H5NH3+Cl-

base          acid                 salt

  • Like ammonium salts, amine salts are soluble ionic compounds, so when the alkyl group is small they are water soluble but become less so as the carbon chain increases

  • We can show the reaction in Brønsted-Lowry terms, where ammonia or the amine acts as a proton acceptor:

Ammonia acting as a Brønsted-Lowry base

Nitrogen Compounds - Ammonia and Amines as Bases, downloadable AS & A Level Chemistry revision notes
The nitrogen atom in ammonia and amines can donate its lone pair of electrons to form a bond with a proton and therefore act as a base

Strength of ammonia and amines as bases

  • The strength of amines depends on the ability of the lone pair of electrons on the nitrogen atom to accept a proton and form a dative covalent bond

  • The more readily a proton is attracted, the stronger the base is

  • Factors that may affect the basicity of amines include:

    • Positive inductive effect - Some groups such as alkyl groups donate electron density to the nitrogen atom causing the lone pair of electrons to become more available and therefore increasing the amine’s basicity

    • Delocalisation - The presence of aromatic rings such as the benzene ring causes the lone pair of electrons on the nitrogen atom to be delocalised into the benzene ring

    • The lone pair becomes less available to form a dative covalent bond with ammonia and hence decreases the amine’s basicity

Ethylamine is more basic than phenylamine

Nitrogen Compounds - Ethylamine _ Phenylamine, downloadable AS & A Level Chemistry revision notes
Ethylamine is more basic than phenylamine due to electron donating ethyl group which increases electron density on the nitrogen and makes it more attractive to protons

Decreasing base strength from ethylamine to phenylamine

Nitrogen Compounds - Strength of Bases, downloadable AS & A Level Chemistry revision notes
Phenylamine is a weaker base due to the lone pair on the nitrogen being less available

Examiner Tips and Tricks

Amines have a fishy smell, which disappears as soon as you add an acid, because you are making an non-volatile salt. Decomposing fish give off amines which are produced by the bacterial decomposition of proteins.

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Philippa Platt

Author: Philippa Platt

Expertise: Chemistry

Philippa has worked as a GCSE and A level chemistry teacher and tutor for over thirteen years. She studied chemistry and sport science at Loughborough University graduating in 2007 having also completed her PGCE in science. Throughout her time as a teacher she was incharge of a boarding house for five years and coached many teams in a variety of sports. When not producing resources with the chemistry team, Philippa enjoys being active outside with her young family and is a very keen gardener

Stewart Hird

Author: Stewart Hird

Expertise: Chemistry Lead

Stewart has been an enthusiastic GCSE, IGCSE, A Level and IB teacher for more than 30 years in the UK as well as overseas, and has also been an examiner for IB and A Level. As a long-standing Head of Science, Stewart brings a wealth of experience to creating Topic Questions and revision materials for Save My Exams. Stewart specialises in Chemistry, but has also taught Physics and Environmental Systems and Societies.