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Topic: EAS Reactions : Different Products  (Read 3792 times)

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Offline SVXX

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EAS Reactions : Different Products
« on: June 24, 2010, 03:08:24 PM »


First of all, is this how these reactions proceed?
And secondly, if they do, why do they proceed like this? I thought all electrophilic aromatic substitutions occurred at positions of maximum electron density. There are other positions besides the one the second -R has attacked, and yet this is how these reactions have been given to proceed.
PS : I found this in one of my study packages. 2 mols of ROH have been used in both cases.
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Offline orgopete

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Re: EAS Reactions : Different Products
« Reply #1 on: June 24, 2010, 03:18:07 PM »
…why do they proceed like this? I thought all electrophilic aromatic substitutions occurred at positions of maximum electron density.

This looks like a really good question. I hope someone can post some real data so we might be able to understand the parameters of this reaction. For example, it is known that alkyl groups can be rearranged in Friedel-Crafts types of reactions.
Is this general for all R-groups? How selective is this? Can you effect a 1,6-addition by starting with BF3 and then using AlCl3 for a second substitution reaction?
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Offline SVXX

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Re: EAS Reactions : Different Products
« Reply #2 on: June 24, 2010, 03:31:51 PM »
They haven't given any other such reactions or what would happen otherwise(such as BF3 first and AlCl3 later) orgopete. My study material isn't so deep, unfortunately. I think this must be a general case for all alkyl groups, as cation rearrangement does not influence the site of attack. It merely generates different products as per different positions of the positive charge, and the most stable carbocation ends up giving the major product.
My worry is regarding the sites of attack of the alkyl cations. Why this and not some other sites?
« Last Edit: June 24, 2010, 04:22:15 PM by SVXX »
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Offline SVXX

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Re: EAS Reactions : Different Products
« Reply #3 on: June 25, 2010, 02:34:01 PM »
Some help here please?
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