Comments on: Alcohols – Acidity and Basicity

By: The Best Alkaline Foods and their Health Benefits - Nutritional Direct

The Best Alkaline Foods and their Health Benefits - Nutritional Direct — Sat, 09 Sep 2023 02:52:57 +0000

[…] Alcohol is acidic and can disrupt the body’s pH balance.Opens in a new windowwww.masterorganicchemistry.comAcidic […]

By: James Ashenhurst

James Ashenhurst — Mon, 13 Jun 2022 18:19:47 +0000

In reply to Peter W. Correct me if I have the wrong person, but I believe you have been commenting on this very topic for over 10 years. Do you have an article that you might recommend I could direct my readers to so that they could be more fully informed on this point. Thank you.

By: Peter W

Peter W — Wed, 08 Jun 2022 23:23:03 +0000

While some may think the difference in acidity of trichloro v trifluoroethanol is trivial, I think it is the norm. Can anyone give me one example in which a fluoro substituent is a better electron withdrawer than a chlorine, except for haloacetic acids. If you wish to refer to the haloacetic acids, then please explain the acidity of the substituents of substituted acetic acids as a class.

By: Hina Sarfraz

Hina Sarfraz — Thu, 12 Aug 2021 05:33:11 +0000

This is the great conceptual website which give proper guidness and understanding about the reactions.greatly thanks sir .excellent work

By: Yves de Montaudouin

Yves de Montaudouin — Fri, 22 May 2020 18:02:40 +0000

Esterification-hydrolysis is definitely an equilibrium. If you do not drive the reaction you end up in the middle.
I agree that it is not a purely acid base reaction, but there is definitely an acid base component in it, and this is why you need an acid or a base to at least start it up.
But I see your point, If you have a simple acid base reaction in a close container it is correct.
I have a more serious question ( I am not a chemist ).
In the Fischer esterification reaction, the first step is a protonation at the oxygen of the carbonyl group. I think this step is highly unfavorable. It amount to move the equilibrium to an enol, or to consider the pKa of RCO2H2+ which would be a very very strong acid.
My first question is:
Why don’t we do the nucleophile attack FIRST, and the protonation AFTER on the side of the O-. It looks more favorable.
My second question is:
Chemists seems to have no problem making an alkoxy anion leave the tetrahedral intermediate, but it seems to be a big mistake to make an hydroxy anion leave. Why?
The pKa of their conjugate acid is about the same.
Note: Your web site is wonderful.

By: James Ashenhurst

James Ashenhurst — Fri, 22 May 2020 16:39:03 +0000

In reply to Yves de Montaudouin. Ester hydrolysis (and its opposite, Fischer esterification) are not acid-base equilibria. This post is about simple acid-base reactions where the only bonds forming and breaking are to hydrogen.

By: Yves de Montaudouin

Yves de Montaudouin — Fri, 22 May 2020 14:57:15 +0000

I am not convinced that we should learn:
Stronger Acid + Stronger Base –> Weaker Acid + Weaker Base
It depends on other factors.
For instance:
Hydrolysis of an ester. You start with water (pKa = 16) and an ester and end up with a carboxylic acid (pKa = 4) and an alcohol.
Or you leave a nice glass of wine on Friday night to find vinegar on Saturday morning.

By: James Ashenhurst

James Ashenhurst — Mon, 02 Mar 2020 18:01:08 +0000

In reply to Ashutosh. What do you think, based on a pKa table?

By: Ashutosh

Ashutosh — Thu, 27 Feb 2020 20:40:05 +0000

What is more acidic alkene or alcohol?

By: James Ashenhurst

James Ashenhurst — Fri, 30 Aug 2019 01:58:16 +0000

In reply to Amr. Think about how alkyl groups affect the electron-richness of the alcohol, relative to hydrogen. Are they electron donors or electron acceptors? Do they make it more electron rich or less electron rich? One of the key factors affecting acidity is the stability of the conjugate base, which in this case will be an alkoxide (O-). The oxygen already has a negative charge. What will electron donors do to that negative charge? Make it bigger or smaller? And what do you think is more stable, a larger charge, or a smaller charge? If the charge is less stable, that means that the conjugate base will be more basic, which means that the parent alcohol will be less acidic.