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reaction mechanism
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Humr:
Hello. I am preparing for upcoming exam and i would like to ask if somebody know mechanism of this reaction. I dont like hard memorizing things and i would like to understand it.
Hunter2:
Check keywords Schiff base, Beckmann conversion, enamine,
hollytara:
I'm not sure what the "T" over the reaction arrow means....
I can see the reaction going in acid.
Protonate the C-N double bond on N. This generates carbocation on carbon of C double bond,
Carbocation rearranges. The most stable carbocation has cation adjacent to O. 5 membered ring bond to carbon with hydroxyl breaks and shifts over to the cation C (formerly part of C-N bond). This new carbocation has the 6 membered ring and the + charge where the OH attaches.
The OH loses H as H+ and the C=O bond forms.
Babcock_Hall:
@OP, In general we expect to see your attempt at solving a problem before we can help you. You have been given a generous number of hints.
Humr:
Thanks for suggestions. Explanation by hollytara looks understandable, but it should be done only by heating in decalin. T over arrow means reaction is heated. Also i dont expect to find exact conditions for preparation of ilegal substance.
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