wormulon
Harmless
Posts: 2
Registered: 23-1-2014
Member Is Offline
Mood: No Mood
|
|
Reaction of halogen ketones with ammonia
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.
Google Translate
|
|
|
TheChemiKid
Hazard to Others
Posts: 493
Registered: 5-8-2013
Location: ̿̿ ̿̿ ̿'̿'̵͇̿̿з=༼ ▀̿̿Ĺ̯̿̿▀̿ ̿ ༽
Member Is Offline
Mood: No Mood
|
|
what is monohlorketoni? Do you mean a monochloroketone such as chloropropanone (chloroacetone)?
When the police come
\( * O * )/ ̿̿ ̿̿ ̿'̿'̵͇̿̿з=༼ ▀̿̿Ĺ̯̿̿▀̿ ̿ ༽
|
|
|
wormulon
Harmless
Posts: 2
Registered: 23-1-2014
Member Is Offline
Mood: No Mood
|
|
I mean aliphatic and araliphatic monochloro (halo) ketones.
I use google translation, because my English is not good.
|
|
|
confused
Hazard to Others
Posts: 244
Registered: 17-3-2013
Location: Singapore
Member Is Offline
Mood: tired
|
|
The rection should be something like this
not really sure though, my organic chemistry, isn't all that good
|
|
|
Metacelsus
International Hazard
Posts: 2531
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
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.
|
|
|
bfesser
|
Thread Moved
27-1-2014 at 17:48 |
confused
Hazard to Others
Posts: 244
Registered: 17-3-2013
Location: Singapore
Member Is Offline
Mood: tired
|
|
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
International Hazard
Posts: 1939
Registered: 23-11-2008
Member Is Offline
Mood: Manic Expressive
|
|
Why would the Ammonia not for an imine with the Ketone?
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
|
|
|
Nicodem
Super Moderator
Posts: 4230
Registered: 28-12-2004
Member Is Offline
Mood: No Mood
|
|
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.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
