Chemical Acidity
Although these compounds are related to the ordinary carboxylic acids, and therefore are weak acids, their chemical structure allows for the formation of an internal hydrogen bond between the hydrogen at the hydroxyl group and one of the oxygen atoms of the carboxylic group. Two effects emerge from this situation:
- Due to the "occupation" of electrons of the carboxylic oxygens in the hydrogen bonding, the acidic proton is held less strongly, as the same electrons are used in bonding that hydrogen too. So the pKa of 2-hydroxypropanoic acid (lactic acid) is a full unit lower compared to that of propionic acid itself (3.86 versus 4.87)
- The internal bridging hydrogen is locked in its place on the NMR timescale: in mandelic acid (2-hydroxy-2-phenylacetic acid) this proton couples to the one on carbon in the same way and magnitude as hydrogens on geminal carbon atoms.
Read more about this topic: Hydroxy Acids
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