October 18, 2024, 12:31:44 PM
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Topic: Nitration of dimethylaminebenzene  (Read 3896 times)

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Offline Berettagtz

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Nitration of dimethylaminebenzene
« on: March 25, 2008, 12:00:09 AM »
Can someone tell me why does the nitration of dimethylamine benzene procede meta instead of ortho para?

I thought -N(CH3)2 was an ortho para director.

Thanks in advance.

Offline macman104

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Re: Nitration of dimethylaminebenzene
« Reply #1 on: March 25, 2008, 12:31:31 AM »
-N(CH3)2 is ortho/para directing.  However, I suppose it's possible that the amine could be become protonated.  If that happens, then it goes from being ortho/para to meta directing.

Offline Berettagtz

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Re: Nitration of dimethylaminebenzene
« Reply #2 on: March 25, 2008, 02:21:33 AM »
So, once the amine gets protonated, it will then become an electron withrdrawing group.  And that will make it a meta director. 
is that correct?

Offline macman104

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Re: Nitration of dimethylaminebenzene
« Reply #3 on: March 25, 2008, 03:25:49 AM »
Yes, I am only making a guess.  Assuming the nitration does proceed with the meta isomer being formed like you said and not the ortho/para products (which would have been my initial guess), that would be my rationalization.

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