Some Important Acids Acetic acid is in vinegar and other foods, used industrially as solvent,catalyst,and reagent for synthesis. Fatty acids from fats and oils. Benzoic acid in drugs,preservatives. Adipic acid used to make nylon 66. 二 Phthalic acid used to make polyesters. 邻苯二甲酸
Some Important Acids ◼Acetic acid is in vinegar and other foods, used industrially as solvent, catalyst, and reagent for synthesis. ◼Fatty acids from fats and oils. ◼Benzoic acid in drugs, preservatives. ◼Adipic acid used to make nylon 66. ◼Phthalic acid used to make polyesters. 邻苯二甲酸 己二酸
Sec 2 PREPARATIONS OF CARBOXYLIC ACIDS Functional group transformations oPrimary alcohols and aldehydes are converted to carboxylic acids by oxidation. oAcid chlorides,acid anhydrides,esters,and amides can be hydrolyzed to their parent carboxylic acids Bond cleavage Cleavage of an alkene with hot KMnO4 produces a carboxylic acid if there is a hydrogen on the double- bonded carbon. Cleavage of an alkyne with ozone or hot permanganate. C-C bond formation Grignard Carboxylation oalkylating diethyl malonate
Sec 2 PREPARATIONS OF CARBOXYLIC ACIDS ◼Functional group transformations ⚫Primary alcohols and aldehydes are converted to carboxylic acids by oxidation. ⚫Acid chlorides, acid anhydrides, esters, and amides can be hydrolyzed to their parent carboxylic acids ◼Bond cleavage ⚫Cleavage of an alkene with hot KMnO4 produces a carboxylic acid if there is a hydrogen on the doublebonded carbon. ⚫Cleavage of an alkyne with ozone or hot permanganate. ◼C-C bond formation ⚫Grignard Carboxylation ⚫alkylating diethyl malonate
RXNs of Carboxylic Acids:An Overview Carboxylic acids transfer a proton to a base to give anions,which are good nucleophiles in SN2 reactions Like ketones,carboxylic acids undergo addition of nucleophiles to the carbonyl group In addition,carboxylic acids undergo other reactions characteristic of neither alcohols nor ketones OH Deprotonation Reduction OH 2004 Tho n/Brooks Cole Alpha substitution Nucleophilic acyl substitution Carboxylic acid
RXNs of Carboxylic Acids: An Overview ◼Carboxylic acids transfer a proton to a base to give anions, which are good nucleophiles in SN2 reactions ◼Like ketones, carboxylic acids undergo addition of nucleophiles to the carbonyl group ◼In addition, carboxylic acids undergo other reactions characteristic of neither alcohols nor ketones
脱羧和还原 R 酸性 羟基被取代 a-H的取代 ■羧酸反应：酸性；成盐反应；衍生物的生成； α一卤代；脱羧反应；还原反应
◼羧酸反应：酸性；成盐反应；衍生物的生成； －卤代；脱羧反应；还原反应 酸性 羟基被取代 脱羧和还原 -H的取代 R CH C O H H O