tailieunhanh - Chapter 12: CARBOXYLIC ACIDS

IUPAC names: hydrocarbon + “oic acid”. Some natural occurring acids & derivatives. From Grignard reagents. From nitriles: Have 1 more carbon as compared to the halide. | ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@ Chapter 12: CARBOXYLIC ACIDS C=O C=C SP2 carbon Y=OH NOMENCLATURE OF CARBOXYLIC ACIDS IUPAC names: hydrocarbon + “oic acid” Some natural occurring acids & derivatives PREPARATIONS OF CARBOXYLIC ACIDS From Grignard reagents From nitriles Have 1 more carbon as compared to the halide From primary alcohols Can NOT be isolated PCC: pyridinium chlorochromate From aldehydes Aldehydes are generally easier to oxidize than primary alcohols From alkylbenzenes REACTIONS OF CARBOXYLIC ACIDS Esterification reactions IUPAC names: alkyl + carboxylate Intramolecular ester formation: Lactones IUPAC names: 2-oxacycloalkanone Reactions of esters Ester hydrolysis Transesterification reactions Acyl chloride formation IUPAC names: replace “ic acid” with “yl halide” / “carboxylic acid” with “carbonyl halide” Reactions of acyl chlorides An amide Amide formation IUPAC names: replace “ic acid”, “oic acid”, “ylic acid” with “amide” Reactions of amides Reaction only in the presence of an acid The Hell-Vohard-Zelinski reaction Radical substitution (halogenation) will occurs in the absence of PBr3, P Only for a-hydrogens Reaction mechanism: Reduction reactions H2/Ni, Pt, Pd or NaBH4 can NOT reduce acids, esters, amides LiAlH4 is used to reduce only compounds such as acids, esters, amides that can NOT be reduced by milder agents | ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@ Chapter 12: CARBOXYLIC ACIDS C=O C=C SP2 carbon Y=OH NOMENCLATURE OF CARBOXYLIC ACIDS IUPAC names: hydrocarbon + “oic acid” Some natural occurring acids & derivatives PREPARATIONS OF CARBOXYLIC ACIDS From Grignard reagents From nitriles Have 1 more carbon as compared to the halide From primary alcohols Can NOT be isolated PCC: pyridinium chlorochromate From aldehydes Aldehydes are generally easier to oxidize than primary alcohols From alkylbenzenes REACTIONS OF CARBOXYLIC ACIDS Esterification reactions IUPAC names: alkyl + carboxylate Intramolecular ester formation: Lactones IUPAC names: 2-oxacycloalkanone Reactions of esters Ester hydrolysis Transesterification reactions Acyl chloride formation IUPAC names: replace “ic acid” with “yl .