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

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SUMMARY

Lactic acid (C3H6O3), which contains both a carboxyl group and a hydroxyl group, can react with sodium hydroxide (NaOH). However, while the carboxyl group will neutralize with NaOH, the hydroxyl group will not react under standard conditions. A stronger base than NaOH is required to deprotonate both functional groups simultaneously. Thus, the reaction of lactic acid with NaOH results in the neutralization of the carboxyl group only, producing water and a salt.

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

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