Chemguide: Support for CIE A level Chemistry
Learning outcome 33: Carboxylic acids and derivatives
33.3: Acyl chlorides
Learning outcome 33.3.3
This statement asks for the mechanisms for all the reactions you will have met in statement 33.3.2. These are the reactions between acyl chlorides and water, alcohols, phenol, ammonia and primary and secondary amines.
Start by reading this page which is an introduction to these reactions.
It is really important that you understand this general case of a nucleophilic addition-elimination reaction before you go on to look at specific examples.
When you are sure about this, work your way through the nucleophilic addition-elimination reaction menu which covers (nearly) all of these reactions. Don't forget to look at the "Help!" pages as well.
If you find this boringly repetitive, that's good! If you understand what you are doing, it is boringly repetitive.
Remember that in the cases of ammonia and the amines, CIE expect you to stop when you get the organic product and HCl. Ignore any further reactions involving the HCl.
You can also stop at the point in all the cases involving nitrogen where the hydrogen ion is removed by a chloride ion. Because CIE want the formation of HCl in all these reactions, they won't expect the alternatives (invoIving removal by ammonia or the amine) I give on this page.
The only thing missing from those pages is the reaction with a secondary amine. This is exactly like the reaction with primary amines, except that there is an extra hydrocarbon group attached to the nitrogen in place of one of the hydrogens.
Work out the mechanism for yourself using a simple secondary amine like (CH3)2NH. Don't just do it in your head - write it out in full in the same way that all the other mechanisms are written.
© Jim Clark 2020