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Topic: Increasing Basicity  (Read 3517 times)

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Offline MichaelWestin

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Increasing Basicity
« on: May 04, 2010, 01:29:44 AM »
Which of the following is the most basic? Which is the least?

Benzylamine
m-chlorobenzylamine
m-ethylbenzylamine
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Offline NahiEw

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Re: Increasing Basicity
« Reply #1 on: May 05, 2010, 02:44:32 AM »
Consider inductive effect for each of the molecules and how it affects the area where it would be most basic, namely nitrogen. Would an electron withdrawing group attached to the amine be more or less basic?
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Offline Nemesisof99

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Re: Increasing Basicity
« Reply #2 on: May 05, 2010, 04:02:32 AM »
An ethyl group is an electron donating group, so it should increase the availability of the lone pair on nitrogen, thereby increasing its basicity. A chloro group is electron withdrawing by inductive effect.
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