[redballoons]

Starting with succinic anhydride, give the reagents and/or conditions necessary to produce...

NH₄⁺-OOCCH₂CH₂CONH₂



First I would added H₂O/H⁺ to the succinic anhydride to open the ring and give...

HOOCCH₂CH₂COOH


Then I would add NH₃...

This is where I'm getting confused because I have two mechanisms in my notes for adding NH₃ to a carboxylic acid.

1.) R-COOH + NH₃  R-COO-NH₄⁺ (used during imide formation)

2.) R-COOH + HNR₂  R-CONR₂ (used during amide formation)


Which one is right?
And how can I get CONH₂ at one end but COO-NH₄ at the other?

[redballoons]

Ok so I have done some more research and I would still add H₂O/H⁺ to get...

HOOCCH2CH2COOH

Then I would add SOCl₂ R-COCl

Then I would add NH₃  R-COO^-NH₄⁺ + HCl

Then I could heat it  R-CONH₂ + H₂O

But is there a way to protect one end so that it doesn't go from R-COO^-NH₄⁺ to R-CONH₂ when heated?


Or am I making this way more difficult then it really is?
Would adding 2NH₃ to succinic anhydride  result in the desired product? It would have a similar reaction to the addition of concentrated ammonia solution added to ethanoic anhydride.

[ashmus]

Going back, are you certain the following reaction will equate to the carboxylate ammonium salt? Go through the mechanism. What is the nucleophile and what is the electrophile?

RCOCl + NH₃  R-COO^-NH₄⁺

You were making it a bit more complicated, but it seems you now managed to make your compound in one step. 

[discodermolide]

Why not just use concentrated ammonia?

[orgopete]

Hint, I think the answer could be the reaction of two equivalents of ammonia with succinct anhydride. Can you determine why this might succeed?