Why isn't this an amide?

[MedPR]

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I'm going to write this out as it is bonded to make it simpler.

H2N-CO-CH2-CH2NH2

I thought an amide was a carbonyl with an amine bound to it - H2NCOR?


This is example 7.9 in TBR organic chem 2. Page 165.

 

[411309]

That looks like an amide to me 😵. C double O with NH2 dunno how it's not.

 

[milski]

It certainly has an amide functional group. Could it be that amines have higher precedence on IUPAC, making the whole molecule an amine and not amide???


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[MedPR]

Well the question is a "which of the following is the major product of this reaction?"

TBR ruled out the one in the OP because "amines react with esters to yield amides, so C is elminated"

The correct answer is H2N-CO-CH2-CH2OH

I don't know how to name the substrate in the reaction, but it is a cyclobutanone, but instead of 2 alpha carbons, there is one alpha carbon and one oxygen in the ring.

It reacts with an NH3.

 

[milski]

Actually, amides have the same priority as carboxylic acids, so the first compound should be some sort of 3-amine-amide. Probably a sloppy explanation in their answer - most likely they expect you to know that you'll get an OH instead of the NH3 at one end. 😕

 

[MedPR]

Actually, amides have the same priority as carboxylic acids, so the first compound should be some sort of 3-amine-amide. Probably a sloppy explanation in their answer - most likely they expect you to know that you'll get an OH instead of the NH3 at one end. 😕

How do I know that NH3 won't displace the OH and add on as an NH2? Is it because OH is a stronger base than NH3? Stronger base = less stable = worse leaving group?