Organic compounds containing oxygen Matej Kohutiar http://www.wellesley.edu/Chemistry/chem227/lipids/transport.htm
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Organic compounds containing
oxygen
Matej Kohutiar
http://www.wellesley.edu/Chemistry/chem227/lipids/transport.htm
Organic compounds containing
oxygen
• Alcohols and phenols
• Carbonyl compounds
• Carboxylic acids and derivatives
• Ethers
Electron configuration of oxygen
1s2 2s2 2p4
In organic molecule oxygen is attached covalently
O
O
Electronic effects in molecules
Inductive effect
H3Cδ δ+ →CH2
δ+ → Cl δ-
Hydroxy derivatives
• Alcohols (Csp3-OH)
• Phenols (Car-OH)
• Ethers (R-O-R)
Alcohols
-Cδ+→O δ -←Hδ+
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)
Alcohols
The number of hydroxyl groups, there are:
• Monohydroxyderivatives
• Polyhydroxy alcohols
Diols (dihydroxyderivatives,)
Triols (trihydroxyderivatives)
Tetrols (tetrahydroxyderivatives)
• Phenols -OH attached primary to aromatic ring
Acidity and alkalinity
CH3
OH
NaNH2CH3
O Na
CH3
OH
NaOH CH3
ONa
Acidity and alkalinity
OH2OH
-
CH3
OH
CH3
CH3
OH
CH3
CH3
OHCH3
CH3
O-
CH3
O-
CH3
CH3
O-
CH3 CH3
acidity
alkalinity
Nucleophilic substitution
CH3
OH
H+
CH3
OH2
+
CH3
Nu
Nu
Nucleophilic substitution
CH3
CH3
OH ClHCl
CH3
CH3
CH3
CH3
OH
CH3
CH3
BrPBr3
Elimination
CH3
OH
CH3H3PO4
OH
CH3
H2SO4
CH3
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
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
PHENOLS
Phenols
OH O-
Reactions of phenols
OH OH
N+
O-
O
OH
N+
O-
O
N+
O-
O
HNO3
H2SO4
ONa
CO2
OH
C
O
OH
Reactions of phenols
OH
OHC
C
O
O
OH
OH
C
C
O
O
K2Cr2O7
K2Cr2O7
Biological effects of phenols
• Reactive group of acidic properties
• Phenol
• Resorcine
• Salicylic acid
• Acetylsalicylic acid
CARBONYL COMPOUNDS
O
CH3
muscone
CH3
CH3
CH3
O
citral
O
OH
O
CH3
vanil in
O
cinnamaldehyde
Reactivity
C O
R1
R1
+ -
Nucleophilic addition
O
R
R1
Nu-
O-
R
R1
NuH
+
OH
R
R1
Nu
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
Nucleophilic addition
CH3 C
CH3
ONH2-CH3
CH3
CCH3
NH
CH3
OH
CH3
C
CH3
NH
CH3
OH -H2OCH3 C
CH3
N
CH3
Aldol condensation
C
R2
R1
H
O
+
-
Aldol condensation
CH3 CH
O+ CH3
CH OCH3
CH
O
OH
Biological effects of carbonyl
containing molecules
• Very reactive group
• Formaldehyde
• Benzaldehyde
• Acetone
• Steroid hormones
CH3
OCCH3
N
CH3
CH3
NH
CH3
O
O
NN
CH3
CH3NCH3
CH3
O
glutethimid
aminophenazone
methadone
CARBOXYLIC ACIDS
Carboxylic acids
C3+
C3+
C
O H
R
O.
.
. .C
O
O H
R
+
-
+
-
Nucleophilic substitution
esterification
CH3 C
O
OH
C2H5OH+ CH3
C O
O
CH3
Carboxylic Acid Derivatives
Functional derivatives
CR
X
ONu
CR
Nu
O
CR
Cl
O
CR
OCOR
O
CR
OR
O
CR
O
NH2
CR
OH
O
Substitutional derivatives
CH3
C O
OH
Br
C O
OH
OH
CH3 C
C O
OH
O
C
O
NH2
OHCH3C
O
NH2
CH3OH
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
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
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