Lactic Acid and Sodium Hydroxide: Can Both Functional Groups React?

[Stanik]

Hello

This is quite a simple question, but I am hoping someone has the time to help me with this.

So, I have a question relating to lactic acid. Lactic acid (C3H6O3) -or 2-hydroxypropanoic acid- obviously has both a carboxyl group and a hydroxyl group. Now here's my question, should lactic acid react with sodium hydroxide (NaOH), are there any kinds of circumstances where *both* the carboxyl group and hydroxyl group would react with the sodium hydroxide? Obviously the carboxyl group becomes neutralized by the sodium hydroxide, but is there any kind of a situation where the hydroxyl group would react with the sodium hydroxide?
So the formula would be :
lactic acid + 2 NaOH -> product + 2 H20

Possible?
Thank you

 

[movies]

You'd need a stronger base than NaOH to deprotonate both the acid and the alcohol.

 

[ravenprp]

for your question! Yes, it is possible for both the carboxyl group and the hydroxyl group of lactic acid to react with sodium hydroxide under certain circumstances. This reaction is known as esterification and occurs when an acid (in this case, lactic acid) reacts with an alcohol (in this case, the hydroxyl group of lactic acid) in the presence of a base (in this case, sodium hydroxide). The result of this reaction is the formation of an ester and water. In the case of lactic acid, the ester formed would be sodium lactate. So, to answer your question, yes, it is possible for both the carboxyl group and the hydroxyl group of lactic acid to react with sodium hydroxide under certain conditions. I hope this helps!