Unit 4 AQA Acylation and (amide + sodium hydroxide)

I'm looking at the mechanism in which an amine reacts with an acid chloride (methylamine is reacting with ethanoyl chloride). Next to this it says "Hint: the amine can be regenerated by reaction with sodium hydroxide" however this is all it says and nothing about this reaction with sodium hydroxide is explained.

In the mechanism we start with ethanoyl chloride and methyl amine and obtain an N-sub. amide (i.e. N-methyl ethanamide) so if we wanted to get our original amine back we would do N-methylethanamide + sodium hydroxide ---> one of the products would be methyl amine and what would the other products be

Also they've just put this hint about the regeneration of the amine next to the N-sub amide question but does this generally work for all types of amides i.e. if we take any amide and then add sodium hydroxide we will get an amine?

The fact that they've only put hint and then one sentence without explaining in the book makes it difficult to understand. I can't find anything about it in the spec either :eek2:

(edited 10 years ago)

Reply 1

username1042883

It may be similar to the breakdown of esters (page 76) but I'm not sure. I don't like the AQA books.

If it was, you could end up with sodium ethanoate and methylamine, but I need to check that first.

Edit: I think I'm right. Found this:
http://www.chemguide.co.uk/organicprops/amides/hydrolysis.html

(edited 10 years ago)

Reply 2

CasualSoul