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Common Names of Dicarboxylic Acids Table 15.1
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Table 15-1, p. 612
Common Names of Carboxylic Acids
Table 15.1
HC
OH
O
CH3C
OH
O
CH3CH2C
OH
O
CH3CH2CH2C
OH
O
Formic acid
Acetic acid
Propionic acid
Butyric acid
Common Names of Dicarboxylic Acids
Table 15.1
CC
OH
O
CH2
COH
O
CH2
COH
O
Oxalic acid Malonic acid
Glutaric acidSuccinic acid
HO
O
CO
HO
H2C
CO
HOCH2
COH
OH2C
CH2
CO
HO
p. 614
p. 615
Fig. 15-1, p. 616
p. 616
Table 15-2, p. 615
p. 618
p. 618
Fig. 9-16, p. 338
X + E+ XE
Electrophilic Aromatic Substitution
Fig. 9-16, p. 338
pKa’s of Substituted Benzoic Acids
Lower pKa Higher pKa
XOH
OX
O
OH+
p. 620
Preparation of Carboxylic Acids : Review
1. Oxidation of 1 alcohols:a. b.
p. 620
Preparation of Carboxylic Acids : Review
1. Oxidation of 1 alcohols:a. CrO3, H2SO4b. K2Cr2O7, H3O+
1. Oxidation of 1 alcohols:
p. 620
Preparation of Carboxylic Acids : Review
2. Oxidation of aldehydes:a. b.
1. Oxidation of 1 alcohols:
p. 620
Preparation of Carboxylic Acids : Review
2. Oxidation of aldehydes:a. CrO3, H2SO4b. K2Cr2O7, H3O+
1. Oxidation of 1 alcohols:
p. 620
Preparation of Carboxylic Acids : Review
3. Oxidative cleavagea. of aryl benzenes (sect 9.10):
b. carbon-carbon double bonds : i. ii.
Methyl, 1° , 2°
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
p. 620
Preparation of Carboxylic Acids : Review
3. Oxidative cleavagea. of aryl benzenes (sect 9.10): KMnO4
b. carbon-carbon double bonds : i. ii.
Methyl, 1° , 2°
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
p. 620
Preparation of Carboxylic Acids : Review
3. Oxidative cleavagea. of aryl benzenes (sect 9.10): KMnO4
b. carbon-carbon double bonds : i. (sect 8.8) KMnO4ii.
Methyl, 1° , 2°
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
p. 620
Preparation of Carboxylic Acids : Review
3. Oxidative cleavagea. of aryl benzenes (sect 9.10): KMnO4
b. carbon-carbon double bonds : i. (sect 8.8) KMnO4ii. O3, H2O2
Methyl, 1° , 2°
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
p. 620
Preparation of Carboxylic Acids : Review
3. Oxidative cleavagea. of aryl benzenes (sect 9.10): KMnO4
b. carbon-carbon double bonds : i. (sect 8.8) KMnO4ii. O3, H2O2
Methyl, 1° , 2°
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
O C O
H2O+
p. 620
Preparation of Carboxylic Acids :
1. Oxidative Cleavage:a. O3, H2O2
C CH
CH3CHCH2CH2CH2CH2 H
H
CH3
C OHO
CH3CHCH2CH2CH2CH2
CH3
O COH
OH+
O C O
H2O+
2. Reduction of Carbon Dioxide:a. Examplesb. Mechanismc. Limitations
p. 620
Preparation of Carboxylic Acids :
3. Hydrolysis of Nitrilesa. Examplesb. Limitationsc. Mechanisms
i. Acid catalyzedii. Base catalyzed
p. 620
Preparation of Nitriles
1. From Alkyl Halides
2. From Amides
p. 620
Reactions of Nitriles with Reducing Agents
1. Lithium Aluminum Hydride
2. Grignard Reagents
Fig. 15-4, p. 627
C N
C N
p. 628
Fig. 15-5, p. 628
End
