How To Use A Pka Table

2015.7.30.
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How to Use a pKa Table

by James
in Alcohols, General Chemistry, Organic Chemistry 1, Where Electrons Are
Today well talk about an incredibly important skill that might take some time to grasp
but pays tremendous dividends. Well go through the exact details of how to use a pKa
table. [Background for pKa read this post ] Understanding the proper use of a pKa
table will give you the ability to recognize which acid-base reactions will happen and
which will not. This will come up a lot as you progress through Org 1 and Org 2. It might
be helpful to go back and review some of the factors that affect acidity that were talked
about earlier.
Lets say youre given the following question:
http://www.masterorganicchemistry.com/2010/09/29/howtouseapkatable/
1/16
2015.7.30.
By acidity, were talking about Bronsted acidity here in other words, the ability to
donate a proton.
Lets say were given a pKa table with the following values.
Where do we start with this problem?

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2015.7.30.
1. Remember that a pKa table ranks molecules in order of their acidity, from
strongly acidic (e.g. HCl with pKa of 8) to weakly acidic (e.g. methane, pKa of ~50).
2. What determines whether or not an acid-base reaction will happen in the first
place? We apply the following principle to acid-base reactions: A stronger acid will
tend to react with a stronger base to produce a weaker acid and a weaker base.
3. Its easy enough to use a pKa table to determine acid strength we can see at a
glance that H2O (pKa of 15) is a stronger acid than NH3 (pKa of 38). The question
is, how do we determine base strength?
Heres how we do it.Draw out the conjugate bases of the acids on your pka table by
removing a proton.
E.g. NH3 > NH2(-) or CH4 > CH3 (-).
Heres the key principle: The order of base strength is the inverse of acid strength. The
weaker the acid, the stronger the conjugate base. Using this principle, you can also
use the pKa table to give you the strengths of bases. I call this the inverse pKa table.
Heres a pKa table with the conjugate bases included:
4. Heres how we apply this knowledge to the problem.

Find the acid on the pKa table. Find the base on the inverse pKa table. Do the acid base
reaction that is, add a proton to the base and remove a proton from the acid.
5. Evaluate: Is the new acid stronger or weaker? Is the new base stronger or weaker?
6. Examples.
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Example A : We have CH4 and HO(-) We can find CH4 on the pKa table it has a pKa
of 50. Hydroxide ion, HO(-) is not on the left side of the pKa table, but it is on the
inverse pKa table it is the conjugate base of water, H2O. So CH4 is the acid and HO() is the base in this reaction.
Doing the proposed acid base reaction, we transfer a proton from CH4 to HO (-). The
products of this reaction would therefore be CH3(-) and water.
Now we ask the question how do these compare in strength to our starting acids and
bases? Water has a pKa of ~15, and CH4 has a pKa of 50. Our product is a stronger acid.
From the inverse pKa table, we also note that CH3(-) is a stronger base than HO(). Our
product is a stronger base.
Verdict the reaction wont happen. We need to go to a weaker acid-base pair (see
#2, above). So we write NR.
Heres another example.
Example B Take HCCH and NH2(). HCCH has a pKa of 25; on the other hand,
NH2() is on the conjugate base table. Drawing out the products of the acid base
reaction will give us NH3 (weaker acid than HCCH) and HCC() (weaker base than
NH2(). This reaction will go.
Example C : Take NH3 and HCl. This time, we can find both HCl and NH3 on the pKa
table. But HCl has a pKa of (8) and NH3 has a pKa of 38. HCl will clearly act as an acid
here, and NH3 will act as a base.
We can write out our acid base reaction: HCl + NH3 NH4(+) Cl()
Our acidic product, NH4, has a pKa of 9. Our product is a weaker acid than HCl. Our
basic product, Cl(-) ranks below NH3 on our inverse pKa scale. Our product is a weaker
base than NH3. Conclusion: this reaction is also a go. And, indeed, if you find yourself
in a freezing hut with only a bottle of concentrated HCl and aqueous ammonia to keep
you company, adding them together will definitely warm up your day. This is about the
only situation in which I would recommend this.
Q. How do you deal with a compound that is similar but not on the table? Take
hexane, for instance. Even though it is not technically on the list, its behavior is similar
enough to methane theyre both alkanes, after all that we make the assumption that
the pKas are roughly the same. Similarly, an amine like trimethylamine (NMe3) will have
similar behavior to NH3 in the reaction with HCl.
One final point on the big-picture type view. Note the pattern. The conjugate base of
methane (H3C() ) is strong enough to deprotonate anything below it on the pKa table
(that is, pretty much everything). Methyllithium, CH3Li, is an incredibly strong base.
Conversely, acetylide ion, HCC() is strong enough to effectively deprotonate any acid
with a pKa under ~25, and acetate ion (CH3COO()) is weaker still, only able to
deprotonate any acid with a pKa lower than 5.
4/16
2015.7.30.
Thats why I compare a strong base like methyl lithium to a royal flush in poker it will
essentially defeat any hand (acid) it encounters.
Next Post:A Handy Rule of Thumb for Acid Base Reactions
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Walkthrough of Acid-Base Reactions (3) Acidity Trends
Walkthrough of Acid Base Reactions (2): Basicity
Walkthrough of Acid Base Reactions (1)
Five Key Factors That Influence Acidity
Tagged as: acidity, acids, bases, basicity, conjugate acid, conjugate base, equilibrium, pka
tables, skills, stability
{ 4 comments read them below or add one }
5/16
2015.7.30.
Chemistry user May 28, 2011 at 11:23 pm

Thank you very much! This is a helpful trick for my Organic I exam!
Reply
Arpan May 31, 2013 at 3:13 pm

THANK YOU VERY MUCH
this article has provided a concrete way of judging an acid base reaction for which I
was helplessly struggling
great site
keep maintaining and improving it
Reply
Dayakar September 6, 2013 at 9:27 am

thanks for providing the information about Pka ,it is very useful in the acid base
reactions.
Reply
Robert January 18, 2014 at 5:55 pm

Hi, could I use pka tables to see what pka a Base e.g. must have to deprotonate an
Alkohol. In principle it should be higher than 16.
Reply
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