Chemguide: Support for CIE A level Chemistry

Learning outcome 19.2(b)

This statement is about the reactions of acyl chlorides with alcohols, phenols, ammonia and primary amines. It covers material from statement 17.1(a)(vii) as well as 19.2(b).

This will only be tested in the final exam of a two year course.

Before you go on, you should find and read the statement in your copy of the syllabus.

The reactions with alcohols and phenols

You will find this discussed on the page about the preparation of esters. Concentrate on the reactions using acyl chlorides. Ignore entirely the section about acid anhydrides.

The syllabus specifically mentions phenyl benzoate in statement 17.1(a)(vii) which is about ester formation from acyl chlorides. So make sure you read about and understand this reaction (known as the Schotten-Baumann reaction) on this page under the title "Improving the reactions between phenols and some less reactive acyl chlorides".

Then re-read the page about acyl chlorides and water, alcohols or phenol. You will already have read some of this for the reaction with water. Re-read the whole page, and make sure that you understand the similarity between all these reactions.

Notice that the syllabus talks about "phenols", not "phenol". It would be typical of CIE to ask you a question which involved a more complicated example such as the aspirin one at the bottom of the page. I am not suggesting that it is important for you to learn this example, but it is essential that you understand it.

Ignore any reference to the mechanisms for these reactions for now, although you will need the mechanism for the reaction with water in the next statement.

The reactions with ammonia and primary amines

You probably won't have met primary amines yet in any detail. Their chemistry is covered in Section 20.

These reactions are described on the page about the reaction of acyl chlorides with ammonia or primary amines.

Don't try to short-cut this. Make sure that you understand the simple case with ammonia before you go on to the more complicated-looking reactions with primary amines. You will need to know about both types of primary amine - where the amino group is attached to either an alkyl group or a benzene ring.

This is getting to be a fairly complicated bit of chemistry - take your time over it.

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© Jim Clark 2011 (last modified June 2014)