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Amide Hydrolysis

Hi, if somebody could please draw and upload the mechanism for question 2.3. that will be much appreciated. I know it doesn't ask for the mechanism but I would like it as an example for any similar reactions. Thank you x

Reply 1

Original post
by timeisgoingfast
Hi, if somebody could please draw and upload the mechanism for question 2.3. that will be much appreciated. I know it doesn't ask for the mechanism but I would like it as an example for any similar reactions. Thank you x

Reply 2

Reply 3

Original post
by timeisgoingfast

Don't try learning the mechanisms for amide hydrolysis - there is a good reason they are first year undergraduate material.

It think it is more helpful to identify the important functional group (in this case an amide) and to recognise that when hydrolysed, the products will be similar to the organic compounds from which the amide can be synthesised. As such, you will form an amine (in this case "C6H5NH2", since the nitrogen half of the amide functional group is bonded to the arene) and a carboxylic acid (in this case "CH3(CH2)2NHCH(CH3)COOH", since although you are taught that you cannot synthesise an amide through the direct reaction of an amine and a carboxylic acid, you can react amines with acyl chlorides or acid anhydrides directly. However, since there is water present, these cannot form and so the hydrated equivalent if you will forms and thus you make a carboxylic acid).

You will notice I put the structures of the products in quotation marks. That is because in reality, the nitrogens are likely to be protonated to give the corresponding salts of each product as the solution is acidic. However, this does depend on the concentration of the acid left after hydrolysing the amide (though this is more of a uni level thing to consider) and whether an alkaline workup has been carried out (typically assumed at uni, but not at A level - hence it is sensible to assume that the salt is formed if you do an acidic hydrolysis of an amide at A level). It is also possible that since the carboxylic acid formed in this case contains both an amine group and a carboxyl group, it may form a zwitterion. This is again pH dependent (neutral or near neutral pH typically favours a zwitterion, low pH typically favours protonation of both the -COO^- to -COOH and -NH2 to -NH3^+).
(edited 1 year ago)

Reply 4


Absolute lifesaver, thank you so much for the website. I've favourited it for future revision too
Enjoy Christmas and/or New Years Eve! xx

Reply 5

Original post
by TypicalNerd
Don't try learning the mechanisms for amide hydrolysis - there is a good reason they are first year undergraduate material.
It think it is more helpful to identify the important functional group (in this case an amide) and to recognise that when hydrolysed, the products will be similar to the organic compounds from which the amide can be synthesised. As such, you will form an amine (in this case "C6H5NH2", since the nitrogen half of the amide functional group is bonded to the arene) and a carboxylic acid (in this case "CH3(CH2)2NHCH(CH3)COOH", since although you are taught that you cannot synthesise an amide through the direct reaction of an amine and a carboxylic acid, you can react amines with acyl chlorides or acid anhydrides directly. However, since there is water present, these cannot form and so the hydrated equivalent if you will forms and thus you make a carboxylic acid).
You will notice I put the structures of the products in quotation marks. That is because in reality, the nitrogens are likely to be protonated to give the corresponding salts of each product as the solution is acidic. However, this does depend on the concentration of the acid left after hydrolysing the amide (though this is more of a uni level thing to consider) and whether an alkaline workup has been carried out (typically assumed at uni, but not at A level - hence it is sensible to assume that the salt is formed if you do an acidic hydrolysis of an amide at A level). It is also possible that since the carboxylic acid formed in this case contains both an amine group and a carboxyl group, it may form a zwitterion. This is again pH dependent (neutral or near neutral pH typically favours a zwitterion, low pH typically favours protonation of both the -COO^- to -COOH and -NH2 to -NH3^+).

Thank you for the detailed explanation! I now understand the importance of focusing on the functional group and the types of products formed during hydrolysis. Your point about the possible formation of salts under acidic conditions and the zwitterion behavior of the carboxylic acid is really helpful. I also appreciate the clarification about the synthesis of amides and the role of water in this process. It definitely makes sense that these concepts are introduced at different levels of study.
Absolute lifesaver, thank you so damn much,
Enjoy Christmas and/or New Years Eve! xx

Reply 6


Absolute Lifesaver, thank you so much for the website. I have favourited it for future reference for revision.
Again, thank you so much! Enjoy Christmas and/or New Years Eve! xx

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