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Protonated Ketone
pKa ≈ -7

HCl
pKa ≈ -7

Protonated alcohol
pKa = -2

Hydroxide ion
pKa = 0

Carboxylic acid
pKa ≈ 4-5

Protonated amine
pKa ≈ 9-11

Water
pKa ≈ 14

Alcohol
pKa ≈ 15-16

Aldehyde with alpha carbon
pKa ≈ 17-20

pKa ≈ 25-30
⍺-protons acidity: aldehydes > ketones > ethers > amides

Alkyne
pKa = 25

Amine
pKa ≈ 33-40

pKa ≈ 44

pKa > 60