Chemguide: Support for CIE A level Chemistry

This statement is about the formation of esters from carboxylic acids or acyl chlorides. The acyl chloride reactions will only be examined 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.

I'm not really clear how this statement differs from statement 10.6(b). The chemistry has already been covered in that statement. The only really new thing is the formation of phenyl benzoate from phenol and benzoyl chloride.

The formation of ethyl ethanoate

You will find this discussed on the page about the preparation of esters. If you are in the first year of a two year course, only read the section about making esters from carboxylic acids.

If you are in the final year of the course, read the first part ("The basic reaction") of the acyl chloride section as well.

The formation of phenyl benzoate

Phenol doesn't react with carboxylic acids or acyl chlorides as well as alcohols do. In making phenyl benzoate from phenol and benzoyl chloride, the phenol is made into a better nucleophile by reacting it with sodium hydroxide solution to produce phenoxide ions where there is a full negative charge on the oxygen rather than just a partial negative charge.

You will find this reaction (known as the Schotten-Baumann reaction) on the page about the preparation of esters (see above) under the title "Improving the reactions between phenols and some less reactive acyl chlorides".

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