Oxidation State Of Organic Molecules Page 2
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1
2
3Redox Reagents
M-X species are NOT redox reagents
M = H, Li, MgBr, BH
2
X = F, Cl, Br, I, OH, NH
i
H Br, H OH, H NH
, Na Br, Li N
Pr, R
Si-Cl
2
2
3
Addition or elimination of an M X species
is not a redox reaction
Conversion of M to X is Oxidation
Conversion of X to M is Reduction
X X' Species are typically oxidizing agents
+
-
Ox
Br Br, HO OH, R
N
O
, RS Cl, R
N Cl, RS SR, etc
R M
R X
3
2
Red
Addition of X X' to a double bond is an oxidation
Elimination of X X' to form a double bond is a reduction
Transition metals are more complicated - each
X
X'
one has a favorite redox resting place. For all
Ox
+
X X'
metals the lower oxidation states are reducing
Red
agents. Some elements (among them Cr, Ru,
Mn, Os) have accessible higher oxidation states
M M' Species are typically reducing agents
which behave as oxidizing agents.
H H, R
B H, R
Sn H, (Li Li)
, R
B BR
, etc
2+
3+
6+
2
3
n
2
2
Cr
Cr
Cr
Reductant
Oxidant
Addition of M M' to a double bond is a reduction
2+
Pd°
Pd
Elimination of M M' to form a double bond is an oxidation
Reductant
Oxidant
M
M'
Ox
+
M M'
Red
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