carboxylic acid (R-COOH)
pKa ~5
phenol (Ar-OH)
pKa ~10
alcohol and water (R-OH)
pKa ~15
ketone (alpha hydrogen)
pKa ~20
ester (alpha hydrogen)
pKa ~25
terminal alkyne
pKa ~25
amine (R2N-H)
pKa ~35
alkene (vinylic hydrogen)
pKa ~45
alkane
pKa ~60
beta-diketone (alpha H between carbonyls)
pKa ~10
beta-diester (alpha H between carbonyls)
pKa ~15
ammonium ion (R3-N+-H)
pKa ~10