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Hydrogen
pKa = 36

Sulfuric acid
pKa = -3

Hydrochloric acid
pKa = -7

Hydronium ions and Protonated Alcohols
pKa = -2

Carboxylic acids
pKa = 5

Alcohol and Water
pKa = 16

Phenol
pKa = 9

Protonated Carbonyl Group
Z = H, C, OR, NH2, NHR, NR2
pKa = -5

alkene
pKa = 44

alkane
pKa = 50

ammonium ion
pka 9

protonated amines
pka 11

amine
pka 33

diisopropylamine
pka 36

thiol
pka 10

alkene
pka 44

alkyne
pka 25

amide
pka 15

beta-diketone
pka 9

beta-ketoester
pka 11

Malonate ester
pka 13

Ketone
pka 20

Ester
pka 25