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alkane (sp3)
hexanes
THF
ether
50
alkene/arene (sp2)
45
allylic/benzylic
40
amine
30
hydrogen
DMSO
35
terminal alkyne (sp)
alpha to ester
ethyl acetate
acetonitrile
25
alpha to ketone or aldehyde
acetone
20
alcohols
ethanol
methanol
16
water
14
protonated amines or ammonium
phenol
thiol
10
carboxylic acid
5
hydronium
0
protonated alcohol
-2
protonated ether
-4
protonated carbonyl
-7
inorganic acids
-9
DMF
42