Author Topic: (IV) oxidizers and H2O2 mechanism needed  (Read 2924 times)

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  • Guest
(IV) oxidizers and H2O2 mechanism needed
« on: June 27, 2004, 08:38:00 PM »

Last day I used a route which was from my concurrent imagination.  Aim was to understand the basics of aromatic acylation and oxidationn of benzylic

Starting with o-Toluidine the route was as follows:

Acetylation (N-acetyl ortho Toluidine)
2mls of o-Toluidine was put in a 250ml rbf equipped w/an efficient reflux  condenser, cacl2 moisture protection tube, a pressure equalized addition funnel  and an egg shaped stirbar which was heated by means a silicone oil bath. Stirring started and 5mls of acetyl chloride was slowly added in portions being careful to keep the violent, exhothermic reaction under control. After the adiition was complete the reaction was stirred for a further 2 minutes with heating and when no further HCl formed there was added150mls of H2O slowly, to decompose the excess acetyl chloride and the diacetyl ester of o-Toluidine. The paste like reaction mixture slowly crystallyzed inside the H2O which was brought to a  gentle boil then left to cool  overnigt. Next day the the crystals were iltered to obtain a theoritical amount of odorless,  needle like crystals of unknown purity (Didnt bother w gc/ms)

Oxidation (N-Acetylanthranilic Acid)
The crystals were put inside 20mls of H2O2 . No reaction occured. I instantly got some naoh(1N ) from the shelf and added some into the rxn (I dont know why I did this, its just an instict) the reaction started violently which was cooled w/ an icebath and died off pretty quickly (45min). It was let to cool, the ph was adlusted to 7.3 with HCl and  crystals were preticipated by  addition of acetic acid.  It was left overnigt. Next day crystals were filtered w suction dried in a dessicator to yield an unspecified amount to powder like meterial. It smelled very aromatic and sweet.

-Can o-Toluidine HCl form in the acetylation phase? (the rxn was anhydrous but can HCl react w the amine to form the o-Toluidine HCl?)
-Can H2O2 accomplish the N-acetyl,o-toluidine to N-Acetylanthranilic Acid?
-What is the efftect of the base?(It does accelerate the decomposition of H2O2 but is this important? And why?)
-Does N-Acetylanthranilic Acid or Anthranilic Acid smell  sweet and aromatic as above? Or is it tbe the decomposition product - benzoic acid?
-What is the oxidation mechanism of (IV) oxidizers (permanganates, dichromates) and what do they do that H2O2 cant? -Please show some references for this

Thank you very much for reading!


  • Guest
« Reply #1 on: June 27, 2004, 09:41:00 PM »
First you say

Oxidation (N-Acetylanthranilic Acid)

and then ask

-Can H2O2 accomplish the N-acetyl,o-toluidine to N-Acetylanthranilic Acid?

Now what is the logic in that? Do you know if you have the acid or not? In case there is no literature on the subject and you try the synth for the first time, you either establish the identity of the products yourself or you can expect no answer at all. Many newbees seem the think there is a chemistry god who can predict everything that is going to happen in an ex tempore witches brew, but chemistry is no mathematics, organic chemistry the least.

I suggest you read more chemistry and learn how to find answers to your questions in a university library. Well-prepared questions are more likely to get answered, but if you cannot even provide the basic information about the identity of your substances, melting points of purified samples for example, there is no hope whatsoever. Learn more and never forget to UTFSE.



  • Guest
Chemistry is no mathematics....
« Reply #2 on: June 30, 2004, 11:05:00 PM »
lutesium  see...

Post 516563

(java: "Organic Chemistry Virtual text....", Newbee Forum)

here ia a collection and explanations of the terms you ask about, as for the rest's not clear , state a question at a time once you've exhausted the search function here and on your browser , just so that  you won't get lazy and you just won't learn that way!

MOO A point of clarification......

"chemistry is no mathematics...."

Although chemistry isn't mathematics , organic reactions are explained and predicted in mathematical models and defined in terms, i.e.differential equations , where the parameters are defined, and the constants added. . It's mathematics that explains the energy affinities and probabilities of energy level cloud transitions in chemical bonding in all reactions. One could say chemistry is explained through


  • Guest
Chromium/Manganese Oxidation Mechanisms
« Reply #3 on: July 01, 2004, 06:30:00 AM »


  • Guest
thank you java and Rhodium
« Reply #4 on: July 09, 2004, 09:33:00 PM »