MadSci Network: Chemistry
Query:

Re: Why is ascorbic acid an acid if it has no COOH group?

Date: Fri Dec 14 12:32:58 2001
Posted By: Dan Berger, Faculty Chemistry/Science, Bluffton College
Area of science: Chemistry
ID: 1006721609.Ch
Message:

structure of ascorbic acid
Why is ascorbic acid an acid if it has no COOH group?

I have a student who is comparing ascorbic acid and citric acid as pH modifiers in an experiment to look at denaturing of the bromelain enzyme in pineapple. On consideration of the structure of ascorbic acid to explain its effect, I see it has no carboxyl group, only hydroxyl groups and a carbonyl group. Does the carbonyl group on an adjacent carbon sufficiently withdraw and delocalise electrons to cause the dissociation of the hydroxyl group on the next carbon atom to cause the acidity of ascorbic acid?


You're on the right track.

Acids are stronger if their conjugate bases are more stable. For example, HF is a stronger acid than H2O because F- is a more stable anion than HO-.

One thing that stabilizes anions is delocalization of the negative charge by resonance (compare the acidities of phenol and cyclohexanol, for example). In ascorbate ion (the conjugate base of ascorbic acid), the negative charge is shared between the two oxygens marked in blue on the structure, by way of the intervening carbon atoms:

resonance in ascorbate anion

This stabilization of the anion--similar to that in carboxylic acids--is enough to make ascorbic acid about as acidic as acetic acid.

resonance in acetate anion

Bluffton College
http://www.bluffton.edu/~bergerd



Current Queue | Current Queue for Chemistry | Chemistry archives

Try the links in the MadSci Library for more information on Chemistry.



MadSci Home | Information | Search | Random Knowledge Generator | MadSci Archives | Mad Library | MAD Labs | MAD FAQs | Ask a ? | Join Us! | Help Support MadSci


MadSci Network, webadmin@www.madsci.org
© 1995-2001. All rights reserved.