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3 votes
1 answer
54 views

Will ethyl 2-amino-1H-imidazole-5-carboxylate undergo ester aminlysos with the primary amines of bPEI efficiently in methanol?

I was about to set up the following reaction, but before I do, I wanted to see if anyone has some suggestions or thinks this will not work: 24mmol Nboc protected ethyl 2-amino-1H-imidazole-5-...
toodles's user avatar
  • 137
1 vote
0 answers
1k views

While treating 4-aminophenol with acetic anhydride why does the reaction stop at Paracetamol and does not undergo esterification with acetic acid?

This needs a little background so I will be showing you a question from one of my Organic Chemistry problem books:- Now, the book shows the answer as Option (c) which is Paracetamol. I tried to work ...
Harsh Mishra's user avatar
2 votes
1 answer
3k views

Direct conversion of amides to esters

Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic ...
Alex's user avatar
  • 21
1 vote
2 answers
303 views

Formation of Lactone from 5-amino-decanoic acid?

As expressed in the title, I am trying to figure out how to form a lactone from 5-amino-decanoic acid. The thing that comes to my mind as a start is the attachment of the amino group ($\ce{NH2}$) to ...
Giorgio Vitanza's user avatar
11 votes
1 answer
22k views

Mechanism for formation of amide by reaction of amine with ester

This is the mechanism given in my lecture handout: I have a problem with the third species along. Surely the negatively charged oxygen would protonate before the other oxygen would. Also, why does ...
RobChem's user avatar
  • 9,802