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protonated alcohols
pka<0

pronanted carboxylic acid
pka<0

pronanted carbonyls
pka<0

hydronium ion
pka<0

Strong acids
pka<0

carboxylic acids
pka ≈ 5

ammonium
pka ≈ 10

R — N+H3
pka ≈ 10

^^^
pka ≈ 10

protonated amines
pka ≈ 10

alcohols
pka ≈ 15

water
pka ≈ 15

sp hybridized carbons
pka ≈ 25

^^^
pka ≈ 40

^^^
pka ≈ 40

amines
pka ≈ 40

sp2 hybridized carbons
pka ≈ 44

sp3 hybridized carbons
pka ≈ 60