Oxidation State Of Organic Molecules Page 3
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1
2
3Reagents by Redox and Acid/Base Classes
Oxidizing Agents:
Free Radicals:
.
.
.
.
.
Cl
, Br
, I
(Cl
and Br
both add and abstract H)
Compounds with O-O bonds:
PhC(=O)OOC(=O)Ph, tBuOOtBu (free radical initiators)
O
, RCO
H, H
O
, O
3
3
2
2
2
Halogen molecules and related species:
, Cl-OH, Br-OH (add to π bonds)
Cl
, Br
, I
2
2
2
Metals in high valence states:
KMnO
, CrO
(and other Cr(VI) reagents), OsO
, NalO
, MnO
, Fe(III), Cu(II), Ag(II)
4
3
4
4
2
Reducing Agents:
Hydrogenation:
H
/catalyst (transition metals, esp. Pd, Pt, Ni)
2
Metals:
K°, Na°, Li°, Mg°, Zn°
Hydride Donors:
+
t
+
BH
, LiAlH
, NaBH
, Li
HAl (O
Bu)
, Na
B H
CN
3
4
4
3
3
Inorganic Reducing Agents:
Bisulfite (NaHSO
), Hypophosphorous acid (H
PO
), Thiosulfate (Na
S
O
)
3
3
2
2
2
3
Nucleophiles/Bases:
Anionic
-
Carbon Centered: RLi, RMgX, R
CuLi, N≡C:
2
-
+
-
+
-
Nitrogen Centered: iPr
N
Li
, H
N
M
, N
2
2
3
-
-
-
Oxygen Centered: RO
, HO
,CH
C(=O)O
3
-
-
Sulfur Centered: RS
, N≡C-S
-
-
-
Halogens: Cl
, Br
, I
Neutral
R
N, H
N, ROH, H
O
3
3
2
Acids:
Mineral Acids:
HCIO
, H
SO
, HNO
, HCl, HBr, Hl, H
PO
4
2
4
3
3
4
Strong Organic Acids:
RSO
H, CF
CO
H
3
3
2
Carboxylic Acids:
RCO
H
2
Weaker Organic Acids:
H-C≡N, ROH
Basicity, nucleophilicity, and reducing power do tend to go together; electrons are given up in all three cases. Good
-
-
nucleophiles like I
and RS
can give up one electron to an easily reduced compound as well as act as nucleophiles
(making Y-C bonds). In the same vein, acidity and oxidizing power are related. Some strong acids like HCIO
,
4
HNO
, and H
SO
can oxidize compounds as well as protonate them.
3
2
4
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