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Carboxylic Acids (COOH)
pKa ~4-5

Protonated Carboxylic Acid
pKa < 0

Alcohol (ROH)
pKa ~16-18

Pronated Alcohol
pKa ~ -2.4

Amines (NR3)
pKa ~38-40

Protonated Amines (NR4)
pKa ~ 9-11