Chem 233 (O’Doherty)
Oxidation/Reduction Handout
Oxidation States in Organic Chemistry:
Oxidation reactions are transformations that cross the barrier from left to right.
Reduction reactions are transformations that cross the barrier from right to left.
Reduction
X = Cl, Br, I, OTs
H
H
H
C
H
OH
C
H
H
H
Oxidation
H OH
C
H
OH
–H2O
+H2O
OH
C
HO
OH
H
H
H
–H2O
+H2O
O
O
H
–H2O
+H2O
HO OH
C
HO
OH
O
OH
HO
OH
–H2O
+H2O
O
C
O
X
H
H
C
H
X
H
H
C
X
X
H
X
C
X
X
X
X
C
X
Reactions that do not involve a barrier crossing transformation are thus neither oxidation nor reduction
reactions (e.g., HX addition reactions, HX elimination reactions, substitution reactions RX to RNu).
Oxidation States in Organic Chemistry:
Oxidation reactions are transformations that cross the barrier from left to right.
Reduction reactions are transformations that cross the barrier from right to left.
Reduction
X = Cl, Br, I, OTs
Oxidation
OH
CH3 CH3
CH3
OH
CH3
CH3
OH
+H2O
–H2O
H
H
H
H
+H2O
–H2O
OH
OH
OH
–H2O
+H2O
–H2O
HO
O
CH3
OH
OH
H
+HX
X
CH3
HO
O
O
CH3
–HX
+H2O
OH
OH
OH
H
OH
H
H
HO
H
OH
OH
OH
H
+H2O
–H2O
H
H
OH
+H2O
+H2O
HO
H
–H2O
–H2O
OH
OH
Reactions that do not involve a barrier crossing transformation are thus neither oxidation nor reduction
reactions (e.g., HX addition reactions, HX elimination reactions, substitution reactions RX to RNu).
Oxidation States in Organic Chemistry:
Oxidation reactions are transformations that cross the barrier from left to right.
Reduction reactions are transformations that cross the barrier from right to left.
Reduction
X = Cl, Br, I, OTs
Oxidation
OH
+H2O
–H2O
O
X
X
O
X
O
X
OH
X
+HX
–HX
+HX
–HX
–HX
+HX
X
X
X
X
X
+HX
–HX
+2HX –2HX
+HX
–HX
Reactions that do not involve a barrier crossing transformation are thus neither oxidation nor reduction
reactions (e.g., HX addition reactions, HX elimination reactions, substitution reactions RX to RNu).