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radical stability
next to double bond, tertiary, secondary, primary, on double bond
CH4 pKa
50-60
NH3 pKa
36
H2O pKa
15.7
HF pKa
3.2
HCl pKa
-7
HBr pKa
-8 to -9
HI pKa
-9 to -10
H2C=CH2 pKa
44
benzylic hydrogen pKa
43-44
MeOH pKa
15.5
EtOH pKa
15.9

cyclohexanol pKa
16-18

turtbutyl alcohol pKa
18

phenol pKa
10
MeNH3 pKa
10.6
thiol (S-H) pKa
10
carboxylic acid
2-4
linear
look for sp hybridized atom
bent
look for sp3 w/ two lone pairs
trigonal planar
look for sp2 hybridized atom
trigonal planar
look for sp3 w/ 1 lone pair
tetrahedral (bent, trigonal pyramidal) angle
109.5
trigonal planar angle
120