July 01, 2022, 06:12:45 PM
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Topic: reaction mechanism  (Read 410 times)

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Offline Humr

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reaction mechanism
« on: May 19, 2022, 01:16:48 PM »
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.

Offline Hunter2

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Re: reaction mechanism
« Reply #1 on: May 19, 2022, 03:12:25 PM »
Check keywords  Schiff base, Beckmann conversion, enamine,

Offline hollytara

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Re: reaction mechanism
« Reply #2 on: May 21, 2022, 02:34:52 AM »
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. 

Offline Babcock_Hall

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Re: reaction mechanism
« Reply #3 on: May 21, 2022, 02:41:31 PM »
@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.

Offline Humr

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Re: reaction mechanism
« Reply #4 on: May 29, 2022, 02:12:11 AM »
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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