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protnated alcohols
pKa < 0

protnated carboxylic acids
pKa < 0

protnated carbonyls
pKa < 0

hydronium ion
pKa < 0

strong acids
pKa < 0

carboxylic acids
pKa = 5

ammonium
pKa = 10

R-NH3 +
pKa = 10

R-NH2+ -R
pKa = 10

protonated amines
pKa = 10

alcohols
pKa = 15

water
pKa = 15

sp hybridized carbons
pKa = 25

NH3
pKa = 40

R-NH2
pKa = 40

amines
pKa = 40

sp2 hybridized carbons
pKa = 44

sp3 hybridized carbons
pKa = 60