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Topic: Basicity of organic compounds  (Read 3195 times)

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Offline Jey-Jey

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Basicity of organic compounds
« on: June 17, 2016, 05:19:57 PM »
Hello,
I would really appreciate your help with following questing. In a test in organic chemistry I was asked to classify these organic compounds in order of increasing basicity in aqueous solution:
1.   4-trifluormethylaniline
2.   Tributylamine
3.   Methylamine
4.   Di(dodec-1-yl)amine

I think that the order of 1-3 is correct (3 – most alkaline), but I’m really not sure with 4. This compound should be lipophilic (surfactant maybe?) and I don’t know how it will react in the aqueous solution.
I already asked my friends, but we are all just biology students and thus we have a little problem with that.  :)

Thanks for help and sorry for mistakes, I’m not native speaker.

Offline phth

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Re: Basicity of organic compounds
« Reply #1 on: June 17, 2016, 11:22:30 PM »
4>2>3>1

Offline orthoformate

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Re: Basicity of organic compounds
« Reply #2 on: June 18, 2016, 12:26:20 AM »
I think it should be 2>4>3>1

tertiary>secondary>primary>primary fluorinated phenyl

Can anyone confirm?

Offline kriggy

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Re: Basicity of organic compounds
« Reply #3 on: June 18, 2016, 04:01:50 AM »
Secondary are more basic that tertiary from steric reasons. However, given that there are different alkyl groups on each of the aliphatic amines, it might not be that straightforward, especialy with the didodecylamine

Offline Jey-Jey

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Re: Basicity of organic compounds
« Reply #4 on: June 18, 2016, 04:41:12 AM »
Thank you all very much for your help.  :)

Offline orthoformate

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Re: Basicity of organic compounds
« Reply #5 on: June 18, 2016, 10:21:18 AM »
Secondary are more basic that tertiary from steric reasons. However, given that there are different alkyl groups on each of the aliphatic amines, it might not be that straightforward, especialy with the didodecylamine

Thank you!

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