The Student Room Group

Amines confusion

In my class notes and even online notes it says something along the lines of

"It follows that secondary amines, which have two electron-pushing alkyl groups, are stronger bases than primary amines and that tertiary amines are stronger bases than secondary amines."

however in my AQA textbook (AQA, T Lister and J Renshaw) it says "Secondary alkylamines have two inductive effects and are therefore stronger bases than primary alkylaimnes. However tertiary alkylamines are not stronger bases than secondary ones because they are less soluble in water"

So which is correct? Or have I misinterpreted what the textbook is saying?

Thanks :biggrin:
Original post by Secret.
In my class notes and even online notes it says something along the lines of

"It follows that secondary amines, which have two electron-pushing alkyl groups, are stronger bases than primary amines and that tertiary amines are stronger bases than secondary amines."

however in my AQA textbook (AQA, T Lister and J Renshaw) it says "Secondary alkylamines have two inductive effects and are therefore stronger bases than primary alkylaimnes. However tertiary alkylamines are not stronger bases than secondary ones because they are less soluble in water"

So which is correct? Or have I misinterpreted what the textbook is saying?

Thanks :biggrin:


Best thing to do is look up the actual pKa values:

methylamine: 10.62
dimethylamine: 10.64
trimethylamine: 9.76

ethylamine: 10.63
diethylamine: 10.98
triethylamine: 10.65

So you can see that the secondary amines are slightly more basic than the primary, while the tertiary amines are less basic than the secondary.

ref: http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf
Reply 2
Original post by charco
Best thing to do is look up the actual pKa values:

methylamine: 10.62
dimethylamine: 10.64
trimethylamine: 9.76

ethylamine: 10.63
diethylamine: 10.98
triethylamine: 10.65

So you can see that the secondary amines are slightly more basic than the primary, while the tertiary amines are less basic than the secondary.

ref: http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf



Aah okay thanks!

PRSOM

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