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Organic compounds containing
oxygen
Matej Kohutiar
http://www.wellesley.edu/Chemistry/chem227/lipids/transport.htm
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Organic compounds containing
oxygen
• Alcohols and phenols
• Carbonyl compounds
• Carboxylic acids and derivatives
• Ethers
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Electron configuration of oxygen
1s2 2s2 2p4
In organic molecule oxygen is attached covalently
O
O
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Electronic effects in molecules
Inductive effect
H3Cδ δ+ →CH2
δ+ → Cl δ-
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Hydroxy derivatives
• Alcohols (Csp3-OH)
• Phenols (Car-OH)
• Ethers (R-O-R)
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Alcohols
-Cδ+→O δ -←Hδ+
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Alcohols
• In 1o alcohol, only one carbon atom is attached to the
carbon carrying the -OH group (primary carbon)
• In 2o alcohol two carbon atoms are attached to the
carbon carrying the -OH group (secondary carbon)
• In 3o alcohol three other carbon atoms are attached to
the carbon atom carrying the -OH group (tertiary
carbon)
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Alcohols
The number of hydroxyl groups, there are:
• Monohydroxyderivatives
• Polyhydroxy alcohols
Diols (dihydroxyderivatives,)
Triols (trihydroxyderivatives)
Tetrols (tetrahydroxyderivatives)
• Phenols -OH attached primary to aromatic ring
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Acidity and alkalinity
CH3
OH
NaNH2CH3
O Na
CH3
OH
NaOH CH3
ONa
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Acidity and alkalinity
OH2OH
-
CH3
OH
CH3
CH3
OH
CH3
CH3
OHCH3
CH3
O-
CH3
O-
CH3
CH3
O-
CH3 CH3
acidity
alkalinity
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Nucleophilic substitution
CH3
OH
H+
CH3
OH2
+
CH3
Nu
Nu
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Nucleophilic substitution
CH3
CH3
OH ClHCl
CH3
CH3
CH3
CH3
OH
CH3
CH3
BrPBr3
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Elimination
CH3
OH
CH3H3PO4
OH
CH3
H2SO4
CH3
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Oxidation of alcohols
CH3
CH2OH
CH3
CH O
CH3
C O
OH
KMnO4KMnO4
CH3
CH CH3
OH
CH3
C CH3
O
KMnO4
C OH
CH3
CH3 CH3
KMnO4
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Biological effects of alcohols
• Drugs often contain OH group
• Increase of polarity and solubility in water
• Hypnotic activity decreases from tertiary to primary
alcohol
• Natural structures – steroids, hormones etc.
• Methanol
• Ethanol
• Glycerol
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PHENOLS
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Phenols
OH O-
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Reactions of phenols
OH OH
N+
O-
O
OH
N+
O-
O
N+
O-
O
HNO3
H2SO4
ONa
CO2
OH
C
O
OH
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Reactions of phenols
OH
OHC
C
O
O
OH
OH
C
C
O
O
K2Cr2O7
K2Cr2O7
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Biological effects of phenols
• Reactive group of acidic properties
• Phenol
• Resorcine
• Salicylic acid
• Acetylsalicylic acid
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CARBONYL COMPOUNDS
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O
CH3
muscone
CH3
CH3
CH3
O
citral
O
OH
O
CH3
vanil in
O
cinnamaldehyde
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Reactivity
C O
R1
R1
+ -
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Nucleophilic addition
O
R
R1
Nu-
O-
R
R1
NuH
+
OH
R
R1
Nu
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Nucleophilic addition
5 4
OH OH
CH+
1OH
4
O1
CH3
OH
OH OH
O
H+
5
4
OH OH
CH+
1OH
1
4
O
5
OH
OH
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Nucleophilic addition
CH3 C
CH3
ONH2-CH3
CH3
CCH3
NH
CH3
OH
CH3
C
CH3
NH
CH3
OH -H2OCH3 C
CH3
N
CH3
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Aldol condensation
C
R2
R1
H
O
+
-
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Aldol condensation
CH3 CH
O+ CH3
CH OCH3
CH
O
OH
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Biological effects of carbonyl
containing molecules
• Very reactive group
• Formaldehyde
• Benzaldehyde
• Acetone
• Steroid hormones
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CH3
OCCH3
N
CH3
CH3
NH
CH3
O
O
NN
CH3
CH3NCH3
CH3
O
glutethimid
aminophenazone
methadone
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CARBOXYLIC ACIDS
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Carboxylic acids
C3+
C3+
C
O H
R
O.
.
. .C
O
O H
R
+
-
+
-
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Nucleophilic substitution
esterification
CH3 C
O
OH
C2H5OH+ CH3
C O
O
CH3
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Carboxylic Acid Derivatives
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Functional derivatives
CR
X
ONu
CR
Nu
O
CR
Cl
O
CR
OCOR
O
CR
OR
O
CR
O
NH2
CR
OH
O
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Substitutional derivatives
CH3
C O
OH
Br
C O
OH
OH
CH3 C
C O
OH
O
C
O
NH2
OHCH3C
O
NH2
CH3OH
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Examples of Polyfunctional Carboxylic Acids
HOOC-COOH – oxalic acid HOOC-CH2-COOH – malonic acid
HOOC-CH2-CH2-COOH – succinic acid (citric cycle) HCCO-CH2-CH2-CH2-COOH – glutaric acid
lactic acid
malic acid
citric acid
Dicarboxylic acids
-OH group containing acids
Maleic acid and fumaric acid are geometric isomers
pyruvic oxaloacetic acid
Unsaturated acids
a-ketoglutaric acid
Ketoacids
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Errata
By mistake I wrote wrong formula for resorcinol. Please, find right formula for this
structure below:
BR,
M.K.
OH
OH
OH
OH
resorcinolpyrocatechol