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Topic: Product  (Read 4921 times)

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Offline vhpk

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Product
« on: August 27, 2007, 12:21:05 AM »
What are the products of the reaction between xiclohexene C6H10 and Br2 in the solvent CH3OH beside the main product?
I am wondering that if -OH will be added or -OCH3 will be added ???
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Offline lavoisier

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Re: Product
« Reply #1 on: August 27, 2007, 01:21:07 PM »
Think about the mechanism by which Br2 reacts with the alkene, and you will see there is an intermediate that can react with nucleophiles.
When the nucleophile is bromide anion, you'll get the right product.
What other nucleophiles are present in the reaction mixture? But I guess you actually know the answer.

Just be careful how you dissociate CH3OH! I've seen people failing at job interviews for getting the polarity of bonds wrong...

Offline vhpk

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Re: Product
« Reply #2 on: August 29, 2007, 12:34:40 AM »
The reaction is through the intermediate product that is alken bromonium.
The things I want to ask here, why do we choose -OCH3 but not -OH though they also nucleophilic reagent ???
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Offline Walker

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Re: Product
« Reply #3 on: August 29, 2007, 12:26:38 PM »
CH3O is a stronger reagent in terms of nuclephilicity

Offline lavoisier

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Re: Product
« Reply #4 on: August 30, 2007, 01:04:27 PM »
The reaction is through the intermediate product that is alken bromonium.
The things I want to ask here, why do we choose -OCH3 but not -OH though they also nucleophilic reagent ???
I told you, think about what you have in the mixture.
You don't 'choose' your nucleophile, you either have it or don't have it in there.
You have CH3OH, Br2 and the alkene, plus the product when it's formed and the intermediates like the bromonium, bromide ion, etc.

So where would OH- come from? If you are you thinking of something like:

CH3OH --> CH3+ + OH-

I strongly advise you to check your basics of org.chem.

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