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Vol 3 Ascorbic Acid
Vol 3 Ascorbic Acid
It contains an
adjacent enediol adjacent to the carbonyl. This -C(OH)=C(OH)-C(=O)- structural
pattern is characteristic of reductones, and increases the acidity of one of the
enol hydroxyl groups. The deprotonated conjugate base is the ascorbate anion, which
is stabilized by electron delocalization that results from resonance between two
forms:
Ascorbate resonance.png
For this reason, ascorbic acid is much more acidic than would be expected if the
compound contained only isolated hydroxyl groups.
Salts
The ascorbate anion forms salts, such as sodium ascorbate, calcium ascorbate, and
potassium ascorbate.
Esters
Ascorbic acid can also react with organic acids as an alcohol forming esters such
as ascorbyl palmitate and ascorbyl stearate.
Nucleophilic attack
Ascorbic diketone.png