Sciencemadness Discussion Board

Reaction of halogen ketones with ammonia

wormulon - 27-1-2014 at 10:02

Hello!
I want to ask something about the substitution reaction of the halogen atom in monohlorketoni with
ammonia.
Under what conditions occurs? Can ammonia be replaced by phthalimid? And that will react keto
group (C = O) with ammonia, if used alcoholic ammonia solution, with stirring, in order preparing aminoketone.
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TheChemiKid - 27-1-2014 at 13:33

what is monohlorketoni? Do you mean a monochloroketone such as chloropropanone (chloroacetone)?

wormulon - 27-1-2014 at 14:13

I mean aliphatic and araliphatic monochloro (halo) ketones.
I use google translation, because my English is not good.

confused - 27-1-2014 at 15:47

The rection should be something like this

not really sure though, my organic chemistry, isn't all that good


Untitled.png - 37kB

Metacelsus - 27-1-2014 at 17:25

Reacting with phthalimide, then deprotection, will probably work and produce the primary amine as the sole product (Gabriel reaction). For a more OTC route, you could even use sodium saccharine. I have not found any references for Gabriel reactions on haloketones, but I can't see why they shouldn't work.

Reaction with ammonia is not guaranteed to give exclusively the monosubstituted amine. You would need to use a large excess of ammonia.

confused - 27-1-2014 at 20:45

oh right, because the amine group is nucleophillic and can react with the chloroacetone to form a secondary and tertiary

out of curiosity, how much excess ammonia would be needed to ensure that most of the product is the primary amine?

twice the stochiometric amount?

Sedit - 27-1-2014 at 22:14

Why would the Ammonia not for an imine with the Ketone?

Nicodem - 28-1-2014 at 10:40

Quote: Originally posted by confused  
The rection should be something like this

Certainly not: https://www.sciencemadness.org/whisper/viewthread.php?tid=23...
Quote: Originally posted by wormulon  
Hello!
I want to ask something about the substitution reaction of the halogen atom in monohlorketoni with
ammonia.
Under what conditions occurs? Can ammonia be replaced by phthalimid? And that will react keto
group (C = O) with ammonia, if used alcoholic ammonia solution, with stirring, in order preparing aminoketone.

Is there a reason on why you don't simply check the literature first and ask more detailed question latter? The way you started, this topic is obviously not going anywhere. If you want reasonable answers you better ask reasonable questions, with references, obviously. Read the forum guidelines, if you do not know how to properly present a topic.