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2 votes
0 answers
121 views

Can alkyl halides react with guanidine/guanidino groups?

I wonder how the π delocalization of guanidino groups affects the reactivity of the terminal nitrogens with respect to alkyl halides compared to, say, primary amines?
Mowgli's user avatar
  • 183
6 votes
1 answer
5k views

Selectivity of diazo-coupling with p-amino phenol

I came across this question and I've been thinking about it since, without being able to find a convincing major product. This question is related to one I found on this site, Diazo Coupling reaction ...
Sir Arthur7's user avatar
  • 1,169
5 votes
2 answers
6k views

Reaction of amines with diethyl oxalate (Hofmann amine separation method)

Why does only one molecule of secondary amine react with diethyl oxalate and two molecules of primary amine react with diethyl oxalate? I feel secondary amine also should have reacted similar to ...
Ritwik Das's user avatar
  • 2,209
4 votes
1 answer
2k views

Is there any reaction between amines and AgNO3?

I found a question in a book about the reaction between $\ce{AgNO3}$ and aromatic/aliphatic amines, but I couldn't find any information about it. What should be the expected reaction mechanism and ...
Rosbie's user avatar
  • 283
2 votes
0 answers
290 views

Primary amine versus phosphoramidate reactivity with succinate esters

I have posted two reactions below. The top reaction is well known and occurs readily and near quantitatively (e.g. in protein modification), while the bottom reaction to my knowledge does not exist in ...
BBftw's user avatar
  • 991
22 votes
4 answers
8k views

Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
claws's user avatar
  • 963