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Topic: Addition of Hydrogen Bromide to Styrene  (Read 6847 times)

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Offline LeiLei

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Addition of Hydrogen Bromide to Styrene
« on: April 16, 2008, 06:26:57 AM »
Can anyone help me with a few things i'm unsure about....?

1) Why is only one product formed?
2) Write a mechanism for the resction
3) Give three methods that you could use to distinguish the possible products.
4) Why add sodium carbonate to the reaction mixture?
5) Suggest a synthesis of the other possible product.

I know i'm asking a lot but i'm really struggling with this one!

Cheers

Offline sjb

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Re: Addition of Hydrogen Bromide to Styrene
« Reply #1 on: April 16, 2008, 06:49:19 AM »
Consider some of the notes at http://www.chemicalforums.com/index.php?topic=23659.msg

though this does not really cover 3 & 4

Perhaps write both possible products and see how they vary for 3 and consider standard work-up procedures for 4

Offline LeiLei

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Re: Addition of Hydrogen Bromide to Styrene
« Reply #2 on: April 16, 2008, 07:16:09 AM »
Ok thanks.... i'll take a look : )

Offline omegasynthesis999

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Re: Addition of Hydrogen Bromide to Styrene
« Reply #3 on: April 16, 2008, 09:21:38 PM »
I think the double bond of styrene attacks the H in the H-Br so as to form a carbocation. You can either form a primary cation or a secondary benzylic which is much more stable (markovnikov). So you probably will get the Br attach at the Benzylic position.

With regards to the sodium carbonate...not sure...but I think that it might be to clump up with the water. You might want that so that you get the Br to react with the carbocation and so you don't form an alcohol.

For recognition you could use H-NMR. Don't know two other techniques...

You can synthesize antimarkovnikov product with peroxides present.

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