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Topic: Nucleophilic substitution  (Read 3737 times)

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Offline Morgrothiel

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Nucleophilic substitution
« on: January 19, 2007, 10:59:54 AM »
I dunno if this is the right place to post this, but I think so :P

I have this task in my book, and I don't know how to solve it:

Which one of these bromides can be expected to give the largest amount of substitution products when reacting with NaOH

The bromides:


I could really need an explanation :)

Thank you for all your help :)

Offline english

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Re: Nucleophilic substitution
« Reply #1 on: January 19, 2007, 11:32:24 AM »
It definitely wouldn't be (c) because that is an aryl bromide (I'm assuming that is a bromide that is being cut off). 

Aryl halides have more electron density around the alpha carbon, that is, the electrophilic portion of the molecule to be substituted.


Is this an SN1 or SN2 reaction? 

You were given this information, right?

Offline Morgrothiel

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Re: Nucleophilic substitution
« Reply #2 on: January 20, 2007, 06:45:46 AM »
I didnt get more information than I gave you. And accordig to the answer sheet the answer is supposed to be d?

Offline english

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Re: Nucleophilic substitution
« Reply #3 on: January 20, 2007, 07:18:46 AM »
Well your base is strong, so that follows SN2 conditions.

The nucleophile is strong enough to readily displace Br. 

Are you sure it says d)?


It looks more like a) to me. 

Offline Morgrothiel

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Re: Nucleophilic substitution
« Reply #4 on: January 20, 2007, 09:17:03 AM »
You are right, it is a, I looked at the wrong task :P

Thanks :)

Offline english

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Re: Nucleophilic substitution
« Reply #5 on: January 20, 2007, 09:25:44 AM »
You are right, it is a, I looked at the wrong task :P

Thanks :)

You understand why I chose a) right?

The alpha carbon in d) has more hindrance as -OH approaches.

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