Textbook Problem 6C.13

Acidity
Basicity
The Conjugate Seesaw

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Mahnoor_Wani_1I
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Textbook Problem 6C.13

Postby Mahnoor_Wani_1I » Tue Jan 19, 2021 6:26 pm

6C.13 Arrange the following bases in order of increasing strength on the basis of the pKa values of their conjugate acids, which are given in parentheses: (a) ammonia (9.26); (b) methylamine (10.56); (c) ethylamine (10.81); (d) aniline (4.63; see Exercise 6C.12).
Is there a simple pattern of strengths?

I understand how to do the first part of the problem: putting in order of strength of basis (high aka value = strong conjugate base). However, I can't seem to find any pattern from the diagrams given in exercise 6c.12. Could someone explain to me what the pattern is?

Marisa Gaitan 2D
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Re: Textbook Problem 6C.13

Postby Marisa Gaitan 2D » Tue Jan 19, 2021 6:34 pm

I was also confused on this. I couldn't find any pattern, but the solutions manual noted that generally, arylamines < ammonia < alkylamines and that methyl < ethyl < etc. I'm not sure if we need to specifically know these patterns, but it gave me a better sense of what question was asking for in the first place. Hope this helps.

Mahnoor_Wani_1I
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Re: Textbook Problem 6C.13

Postby Mahnoor_Wani_1I » Fri Jan 22, 2021 11:32 am

Thank you! That make sense


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