O
O
O
O
O
H OH formic acid
OH
OH
OH
acetic acid propiopic acid butyric acid
1,4-Addtion, Diels-Alder Reaction
第四军医大学药学
Chapter 10 Carboxylic Acids and Substituted Carboxylic Acids
第四军医大学药学
A carboxylic acid consists of three parts: a hydroxyl group, a carbonyl group, and the “remainder.”
COOH
COOH
COOH H3C
COOH
benzoic acid
H2N
OHBiblioteka 4-aminobenzoic acid 2-hydroxybenzoic acid (salicylic acid)
3-methylbenzoic acid (m-toluic acid)
Many simple carboxylic acids have common names accepted by IUPAC
5
3
6
4
1
CO2H
2
(E)-4-Methyl-3-hexenoic acid
H
2
3C C
H
COOH
1
trans-3-Phenyl-2-propenoic acid
第四军医大学药学
Aromatic acids of the form Ar-COOH are named as derivatives of benzoic acid
O
C R OH
O
C OH
Carboxylic acids
O COOH
OH
CO2H
Representation of a carboxyl group
➢ Carboxyl group is usually written –COOH ➢ Aliphatic acids have an alkyl group bonded to -COOH ➢ Aromatic acids have an aryl group ➢ Fatty acids are long-chain aliphatic acids
Attack by Nucleophiles 1. Nucleophilic Addition 2. Reduction 3. Oxidation
第四军医大学药学
Summary
1. Nomenclature and Structure 2. 1.1. Nomenclature: UIPAC names, Common Names 3. 1.2. Structure 4. 2. Physical Properties and Spectroscopy 5. 2.1. Physical Properties 6. 2.2. Spectroscopy: IR, 1HNMR, 13CNMR, MS, UV 7. 3. Chemical Properties: 8. 4. Synthesis of Aldehydes and Ketones 5. α,β-Unsaturated Carbonyl Compounds:
第四军医大学药学
1. Nomenclature
In naming, the carboxyl group takes priority over any of the other functional groups we have discussed
1.1. UIPAC Names: Monocarboxylic acids: ➢ The aliphatic carboxylic acids are named by replacing the ending -e in the name of the alkane by -oic acid ➢ The alkanoic acid stem is numbered by assigning the number 1 to the carboxy carbon ➢ Substituents are labeled along the longest chain incorporating the CO2H group
General consideration:
O C C
H
H: Acidic 1. Enolization 2. Halogenation 3. Haloform reaction 3. Adol Condensation
Attack by Electrophiles (Activate the carbon of carbonyl group)
CO2H
4
HO
H
12 3
CO2H H
trans-3-Methylcyclopentanecarboxylic acid cis-4-Hydroxycyclohexanecarboxylic acid
第四军医大学药学
Unsaturated acids
✓ Unsaturated acids are named using the name of the corresponding alkene, with the final -e replaced by -oic acid. ✓ The carbon chain is numbered starting with the carboxyl carbon, and a number gives the location of the double bond ✓ The stereochemical terms cis and trans (and Z and E) are used as they are with other alkenes
第四军医大学药学
Cycloalkanes with -COOH substituents are generally named as cycloalkanecarboxylic acids
CO2H
CO2H
1 2
3
3,3-Dimethylcyclohexanecarboxylic acid
1-Cyclopentenecarboxylic acid