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Topic: Alkylation of benzene  (Read 3363 times)

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Offline FinEvitable

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Alkylation of benzene
« on: October 25, 2007, 08:40:06 PM »
Hi there i have to look at the alkylation of benzene and i need a bit of help.
Does the chloromethane form the positive ion with the freidel-crafts catalyst the same way in the chlorination of benzene?
I drew out the reaction mechanism but it just didnt look right to me having the CH3+ ion.
Is that right or am i totally off?
thanks

Offline Dan

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Re: Alkylation of benzene
« Reply #1 on: October 26, 2007, 04:12:01 AM »
You are on the right lines, you form a (or increase the existing) partial positive charge on the carbon of chloromethane,rather than a free carbocation. The displacement of chloride by benzene is probably concerted, given the low stability of CH3+.

Then deprotonate and you're there.
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Offline FinEvitable

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Re: Alkylation of benzene
« Reply #2 on: October 26, 2007, 07:28:54 AM »
Thanks for the help :D
Ive drawn it out now showing it destabilizing the benzene ring and it looks right! There may be a few things ive missed out of the mechanism drawing but i can live with that lol thats why im learning.
Thanks again.

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