4/10/24, 7:42 AM The pKa Table Is Your Friend

Master
Organic LOGIN
Chemistry

Home / The pKa Table Is Your Friend

Acid Base Reactions
By James Ashenhurst
The pKa Table Is Your Friend
 Previous  Next 

Last updated: December 29th, 2022 |

The importance of pKa values in organic chemistry can’t be overestimated, in my opinion.
Not
knowing pKa values in organic chemistry is like not knowing the value of the hands in
poker. In this scheme, alkyl anions are the equivalent of the royal flush – they win the proton
from everything underneath them in the table.
Why is pKa so important? Because every nucleophile is potentially a base, and vice versa. If
you have a reaction where it looks like you might get SN2 or E2, look closely first – is there any
chance of a simple acid-base reaction? For instance, take NaOH plus an alkyl thiol, R–SH. Is it
an SN2? Or possibly an E2? Both are incorrect. The reaction that happens is the simplest one –
deprotonation of SH, to provide water and the deprotonated thiol.
Also, the pKatable tells you about leaving group ability. Good leaving groups are weak bases!
If you don’t know the relative values of the pKa‘s of the major functional groups, you’ll be flying
blind in the course. Expect to hit a tree.
PDF VERSION NOW AVAILABLE (click here)

For more complete lists, be sure to check out Evans and Reich. (check out the resources on
Reich’s page by the way – fantastic!) Blessed are the OCD, for they produce the most beautiful
and complete web resources.
https://www.masterorganicchemistry.com/2010/06/18/know-your-pkas/ 1/12
4/10/24, 7:42 AM The pKa Table Is Your Friend

Master
Organic LOGIN
Chemistry

https://www.masterorganicchemistry.com/2010/06/18/know-your-pkas/ 2/12
4/10/24, 7:42 AM The pKa Table Is Your Friend

Master
Organic LOGIN
Chemistry

Notes
Related Articles

What makes a good leaving group?

Acid-Base Reactions: Introducing Ka and pKa
How to Use a pKa Table
Walkthrough of Acid-Base Reactions (3) – Acidity Trends
Five Key Factors That Influence Acidity
Acid Base Practice Problems (MOC Membership)

Comments
Ayush Sharma
August 24, 2023 at 8:43 am
https://www.masterorganicchemistry.com/2010/06/18/know-your-pkas/ 3/12