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Topic: Bromination of this unsymmetrical ketone???  (Read 4405 times)

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Offline fawad0418

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Bromination of this unsymmetrical ketone???
« on: August 20, 2013, 03:50:07 AM »
I was wondering if bromination of this unsymmetrical ketone would result in Product A or Product B or both.... I need Product A but i think major will be Product B...your opinion please

Offline Archer

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Re: Bromination of this unsymmetrical ketone???
« Reply #1 on: August 20, 2013, 06:31:18 AM »
Look at the mechanism for this reaction, does it favour product A or B?
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Offline fawad0418

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Re: Bromination of this unsymmetrical ketone???
« Reply #2 on: August 20, 2013, 11:45:25 AM »
Look at the mechanism for this reaction, does it favour product A or B?
I think hydrogens between phenoxy and carbonyl are more acidic and probably that would lead to product B

Offline AlphaScent

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Re: Bromination of this unsymmetrical ketone???
« Reply #3 on: August 20, 2013, 01:59:55 PM »
This is a great question.  Im pretty sure I know the answer, but a good question I must say.
If you're not part of the solution, then you're part of the precipitate

Offline fawad0418

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Re: Bromination of this unsymmetrical ketone???
« Reply #4 on: August 21, 2013, 12:16:46 AM »
This is a great question.  Im pretty sure I know the answer, but a good question I must say.
thnx...i am expecting the answer aswell.. ??? This will help me planning my synthesis in case i need to find alternate...I think its Product B but i need Product A. I just want to make sure my assumption if it is right or wrong....Since i am in underdevelped country so we dont have much sophisticated facilities like scifinder, reaxy etc.

Offline Archer

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Re: Bromination of this unsymmetrical ketone???
« Reply #5 on: August 21, 2013, 01:18:59 AM »

thnx...i am expecting the answer aswell.


You can keep on expecting.

I wanted you to show the mechanism of this reaction and show why you think that one product would be favoured over another.

This journal may provide some useful insights into the stability of product A.

 http://pubs.rsc.org/en/content/articlelanding/1988/c3/c39880001098
« Last Edit: August 21, 2013, 01:40:55 AM by Archer »
“ I love him. He's hops. He's barley. He's protein. He's a meal. ”

Denis Leary.

Offline Babcock_Hall

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Re: Bromination of this unsymmetrical ketone???
« Reply #6 on: August 21, 2013, 09:25:04 AM »
@OP, According to forum rules, you are supposed to attempt to answer a problem before we answer in detail.

Offline AlphaScent

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Re: Bromination of this unsymmetrical ketone???
« Reply #7 on: August 21, 2013, 10:51:51 AM »
Arhcer, you are too much...

But as these fellow people have stated, we are not going to answer the question for you.  Look at an NBS mechanism for bromination.  I will tell you you that NBS is used an awful lot for allylic bromination.

http://www.masterorganicchemistry.com/2011/06/10/reagent-friday-nbs-n-bromo-succinimide/

If you're not part of the solution, then you're part of the precipitate

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