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Nitration of dimethylaminebenzene
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Topic: Nitration of dimethylaminebenzene (Read 3895 times)
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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.
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macman104
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Re: Nitration of dimethylaminebenzene
«
Reply #1 on:
March 25, 2008, 12:31:31 AM »
-N(CH
3
)
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.
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Berettagtz
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Re: Nitration of dimethylaminebenzene
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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?
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macman104
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Re: Nitration of dimethylaminebenzene
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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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Nitration of dimethylaminebenzene