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Sulfuric Acid, pKa < 0

Toluenesulfonic Acid or Tosic Acid, pKa < 0

Hydrogen Halides, pKa < 0

Hydronium Ion, pKa < 0

Protonated alcohol or Ether, pKa < 0

Nitric acid, pKa < 0

Pyridinium Ion, pKa = 5

Carboxylic Acid, pKa = 4-5

Ammonium Ion, pKa = 9-10

Thiol, pKa = 10

Amide, pKa = 15-17

Water, pKa = 15.7

Alcohol, pKa = 16-18

Ketone, pKa = 20

Ester, pKa = 25

Alkyne, pKa = 25

Amine, pKa = 38

Benzylic Hydrogen, pKa = 41

Allylic Hydrogen, pKa = 43

Aromatic, pKa = 43

Alkene, pKa = 44

Alkane, pKa = 50

Aldehyde, pKa = 50

Ether, pKa = 50

Epoxide, pKa = 50

Nitro, pKa = 8-10

Nitrile, pKa = 9 or 25 ?