lecture 18.3

lecture 18.3 - 18-18-1Organic Organic...

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Unformatted text preview: 18-18-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson18-18-2FunctionalFunctionalDerivatives ofDerivatives ofCarboxylic AcidsCarboxylic Acids18-18-3Reaction with Ammonia, etc.Reaction with Ammonia, etc.Acid halides react with ammonia, 1 amines, and 2 amines to form amides2 moles of the amine are required per mole of acid chlorideClO2NH3NH2ONH4+Cl-++HexanoylchlorideAmmoniaHexanamideAmmoniumchloride18-18-4Reaction with Ammonia, etc.Reaction with Ammonia, etc.Acid anhydrides react with ammonia, and 1 and 2 amines to form amides2 moles of ammonia or amine are requiredCH3COCCH3O O2NH3CH3CNH2OCH3CO-NH4+O++AceticanhydrideAmmoniaAcetamideAmmoniumacetate18-18-5Reaction with Ammonia, etc.Reaction with Ammonia, etc.Esters react with ammonia, and 1 and 2 amines to form amidesesters are less reactive than either acid halides or acid anhydridesAmides do not react with ammonia, or 1 or 2 aminesPhOEtONH3PhNH2OEt OHPhenylacetamideEthyl phenylacetate++Ethanol18-18-6Acid Chlorides with SaltsAcid Chlorides with SaltsAcid chlorides react with salts of carboxylic acids to give anhydrides most commonly used are sodium or potassium salts +Acetyl chlorideSodium benzoateAcetic benzoicanhydride+CH3CCl-OCCH3COCNa+Cl -Na+OOOO18-18-7InterconversionsInterconversions18-18-8Reaction with Grignard ReagentsReaction with Grignard Reagentstreating a formic ester with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 2 alcohol HCOCH3O2RMgXH2O, HClHC-RROHCH3OH+magnesium alkoxide saltA 2 alcoholAn ester offormic acid+18-...
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lecture 18.3 - 18-18-1Organic Organic...

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