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Topic: Allyl bromide reactivity towards alkylation  (Read 4926 times)

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Offline Enantiomer

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Allyl bromide reactivity towards alkylation
« on: November 09, 2009, 11:11:09 PM »
Hey all,
Just a quick question, I'm looking at the last question in a problem set I'm doing and I'm pretty sure I know the answer but I wana be 100% sure before I write it down,
The question is "briefly explain why allyl bromide is more reactive than ethyl bromide toward alkylation of tosylamide anion in acetone?"

My answer is most likely that it will give an improved E/Z selectivity, however I noticed the key word in that question is 'acetone' leading me to believe that the real reason would be that allyl bromide might be slightly more polar then it's ethyl brother.
Is it both of these or just the polarity?  I'm leaning more towards polarization, but hesitant to write it down simply because it sounds slightly boring to me.

Offline azmanam

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Re: Allyl bromide reactivity towards alkylation
« Reply #1 on: November 10, 2009, 06:01:05 AM »
unfortunately, you're barking up the wrong tree.  Tosylamide (RHN-) is a good nucleophile, and acetone (being a polar aprotic solvent) makes nucleophiles even more nucleophilic.  The reaction is going to be an SN2 reaction.  So what makes allyl bromide (CH2=CHCH2Br) a better electrophile toward SN2 than ethyl bromide?
Knowing why you got a question wrong is better than knowing that you got a question right.

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