Oxidation Levels In Organic Chemistry

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Chemistry 333
Oxidation Levels in Organic Chemistry
In general and inorganic chemistry, an oxidation occurs when a system loses one or more electrons.
Conversely, a reduction occurs when a system gains one or more electrons. The terms, "oxidation" and
"reduction", have less precise definitions in organic chemistry. Despite this ambiguity an oxidation can be defined
as a reaction that introduces a more electronegative element to or removes molecular hydrogen from the system. A
reduction is a reaction that removes a more electronegative element from or introduces molecular hydrogen to the
system. Using these definitions, common organic functional groups can be ranked in the following order:
oxidation level
functional groups
examples
4
tetrahaloalkanes
CCl
4
carbon dioxide
CO
2
3
trihaloalkanes
H
CCCl
3
3
carboxylic acids
H
CCOOH
3
carboxylic acid derivatives
esters
H
CCOOCH
3
3
orthoesters
H
CC(OCH
)
3
3
3
acid anhydrides
H
CCOOCOCH
3
3
acid halides
H
CCOCl
3
amides
H
CCON(CH
)
3
3
2
nitriles
H
CC≡N
3
2
dihaloalkanes
H
CCHCl
3
2
alkynes
HC≡CH
ketones
H
CCOCH
3
3
aldehydes
H
CCOH
3
acetals
H
CCH(OCH
)
3
3
2
imines
H
CCH=NCH
3
3
1
monohaloalkanes
H
CCH
Cl
3
2
alkenes
H
C=CH
2
2
alcohols
H
CCH
OH
3
2
ethers
H
CCH
OCH
3
2
3
amines
H
CCH
N(CH
)
3
2
3
2
0
alkanes
H
C-CH
3
3
Note: Each "O" in the table denotes an oxygen that is doubly-bonded to a carbon.

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