Chapter17CarboxylicAcids-精选课件(公开).pptVIP

Chapter 17: Carboxylic Acids Chem 30B Lecture 22 Reaction with Bases Carboxylic acids, whether soluble or insoluble in water, react with NaOH, KOH, and other strong bases to give water-soluble salts. They also form water-soluble salts with ammonia and amines. Reaction with Bases Carboxylic acids react with sodium bicarbonate and sodium carbonate to form water-soluble salts and carbonic acid. Carbonic acid, in turn, breaks down to carbon dioxide and water. Reaction with bases The acid-base properties of carboxylic acids allow an easy separation of carboxylic acids from water-insoluble nonacidic compounds. Preparation Carbonation of Grignard reagents Treatment of a Grignard reagent with carbon dioxide followed by acidification gives a carboxylic acid. Methanol to Acetic Acid Acetic acid is synthesized by carbonylation of methanol. The carbonylation is exothermic. The Monsanto process uses a soluble rhodium(III) salt and HI to catalyze the reaction. Methanol to Acetic Acid Steps 1 and 2: Preparation of the catalyst. Steps 3 and 4: The catalytic cycle. Reduction The carboxyl group is very resistant to reduction. It is not affected by catalytic hydrogenation under conditions that easily reduce aldehydes and ketones to alcohols, and reduce alkenes and alkynes to alkanes. Nor is it reduced by NaBH4. Lithium aluminum hydride reduces a carboxyl group to a 1° alcohol. reduction is carried out in diethyl ether, THF, or other nonreactive, aprotic solvent. Selective Reduction Carboxyl groups are not affected by catalytic reduction under conditions that reduce aldehydes and ketones. Nor are carboxyl groups reduced by NaBH4. Fischer Esterification Esters can be prepared by treating a carboxylic acid with an alcohol in the presence of an acid catalyst, commonly H2SO4, ArSO3H, or gaseous HCl. Fischer Esterification Fischer esterification is an equilibrium reaction. By careful control of experimental conditions, it is possible to prepare esters in high yield. If the