西北农林科技大学：《有机化学 Organic chemistry》课程教学课件（2009）Chapter 11 Carboxylic acids and carboxylic acid derivatives

Carboxylic Acids And Carboxylic Acid ST AAF UN Derivatives Section K

Carboxylic Acids And Carboxylic Acids And Carboxylic Acid Carboxylic Acid Derivatives Derivatives Section K Section K

席林 子h十十 Carboxylic Acids K1 STRUCTURE AND PROPERTIES *K2 NUCLEOPHILIC SUBSTITUTION K3 REACTIVITY K4 PREPARATIONS OF CARBOXYLIC ACIDS K5 PREPARATIONS OF CARBOXYLIC ACID DERIVATIVES K6 REACTIONS K7 ENOLATE REACTIONS

Carboxylic Acids Carboxylic Acids ™K1 STRUCTURE AND PROPERTIES ™K2 NUCLEOPHILIC SUBSTITUTION ™K3 REACTIVITY ™K4 PREPARATIONS OF CARBOXYLIC ACIDS ™K5 PREPARATIONS OF CARBOXYLIC ACID DERIVATIVES ™K6 REACTIONS ™K7 ENOLATE REACTIONS

Look Back to the Nomenclature-IUPAC IUPAC names:drop the -e from the parent alkane and add the suffix -oic acid if the compound contains a carbon-carbon double bond, change the infix -an-to -en- COOH COOH COOH Propenoic acid trans-2-Butenoic acid trans-3-Phenyl- (Acrylic acid) (Crotonic acid) propenoic acid (Cinnamic acid)

Look Back to the Nomenclature - IUPAC ™IUPAC names: drop the - e from the parent alkane and add the suffix -oic acid ‰if the compound contains a carbon-carbon double bond, change the infix -an- to -en￾Propenoic acid (Acrylic acid) trans-3-Phenyl￾propenoic acid (Cinnamic acid) trans-2-Butenoic acid (Crotonic acid) CO O H C 6 H 5 CO O H CO O H

Look Back to the h于十击 Nomenclature IUPAC EST A&F The carboxyl group takes precedence over most other functional groups OH COOH (R)-5-Hydroxyhexanoic acid COOH H2N COOH 5-Oxohexanoic acid 4-Aminobutanoic acid

Look Back to the Nomenclature - IUPAC ™The carboxyl group takes precedence over most other functional groups 5-Oxohexanoic acid 4-Aminobutanoic acid (R)-5-Hydroxyhexanoic acid CO O H OH CO O H H 2N C O O H O

Look Back to the 农林 Nomenclature IUPAC Dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing both carboxyl groups Ethanedioic acid Propanedioic acid (Oxalic acid) (Malonic acid) Butanedioic acid Pentanedioic acid Hexanedioic acid (Succinic acid) (Glutaric acid) (Adipic acid)

Look Back to the Nomenclature - IUPAC ™Dicarboxylic acids: ‰add the suffix -dioic acid to the name of the parent alkane containing both carboxyl groups HO O H O Propanedioic acid (Malonic acid) Ethanedioic acid (Oxalic acid) O HO OH O O Hexanedioic acid (Adipic acid) Pentanedioic acid (Glutaric acid) Butanedioic acid (Succinic acid) O OH O HO OH O HO O HO OH O O

林 Look Back to the Nomenclature IUPAC ST A&F if the carboxyl group is attached to a ring,name the ring compound and add the suffix -carboxylic acid 2 1COOH H. COOH 2-Cyclohexene- trans-1,3-Cyclopentane- carboxylic acid dicarboxylic acid

Look Back to the Nomenclature - IUPAC ™if the carboxyl group is attached to a ring, name the ring compound and add the suffix -carboxylic acid carboxylic acid 3 2 1 2-Cyclohexene￾carboxylic acid trans-1,3-Cyclopentane- dicarboxylic acid CO O H HO O C CO O H

Look Back to the 衣林 Nomenclature IUPAC benzoic acid is the simplest aromatic carboxylic acid use numbers to show the location of substituents COOH COOH COOH COOH OH COOH COOH Benzoic 2-Hydroxybenzoic 1,2-Benzene- 1,4-Benzene- acid acid dicarboxylic acid dicarboxylic acid (Salicylic acid) (Phthalic acid) (Terephthalic acid)

Look Back to the Nomenclature - IUPAC ™benzoic acid is the simplest aromatic carboxylic acid ™use numbers to show the location of substituents Benzoic acid 2-Hydroxybenzoic acid (Salicylic acid) C OOH C OOH OH 1,2-Benzene￾dicarboxylic acid (Phthalic acid) 1,4-Benzene￾dicarboxylic acid (Terephthalic acid) CO O H CO O H CO O H CO O H

东林 Look Back to the Nomenclature IUPAC when common names are used, the letters a,B,Y,δ，etc.are often used to locate substituents 5 1 OH H2N、 OH NH2 4-Aminobutanoic acid 2-Aminopropanoic acid (Y-Aminobutyric acid; (a-Aminopropionic acid; GABA) alanine)

Look Back to the Nomenclature - IUPAC ™when common names are used, the letters α, β, γ, δ, etc. are often used to locate substituents alanine) ( γ-A mi n o b utyr i c acid; ( α-A m i n o p r o pio n i c acid; GABA ) 4-A min o b u tan o i c acid 2-A min o p ro p a n oic acid 4 3 2 5 H 2 N OH O OH O NH 2 OH O α β γ δ 1

More examples CH CH,CH,-COOH Butyric acid（酪酸)：(from Latin butyrum:butter):gives rancid butter its characteristic smell. OH Lactic acid（乳酸)：(from CH CH-COOH Latin lactim:milk):gives sour milk its characteristic taste. CH3(CH2)16-COOH Stearic acid(硬脂酸)：one of the main components of animal fat (saturated fat). OH Citric acid(柠檬酸)gives its characteristic flavor to lemons and HOOC-CH,-C-CH,COOH other citric fruits.Used widely as preservative (antioxidant)and as an COOH additive for tartness

More examples Butyric acid（酪酸）: (from Latin butyrum: butter): gives rancid butter its characteristic smell. Lactic acid （乳酸） : (from Latin lactim: milk): gives sour milk its characteristic taste. Stearic acid（硬脂酸）: one of the main components of animal fat (saturated fat). Citric acid（柠檬酸） gives its characteristic flavor to lemons and other citric fruits. Used widely as preservative (antioxidant) and as an additive for tartness

行十十十十十 ST A&F U acid halide acid anhydride ester 酰卤 酸酐 酯 酰胺 H 1 amide 2°amide 3°amide

R C O X R C O O C O R R C O O R' acid halide acid anhydride ester R C O N H H R C O N R' H R C O N R' R" 1° amide 2° amide 3° amide 酰卤 酸酐 酯 酰胺