ORGANIC CHEMISTRY Dr Nam T S Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 38647256 ext 5681 Email: ptsnam@hcmut.edu.vn 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 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 10 Reactions of esters Ester hydrolysis 16 Transesterification reactions 17 Acyl chloride formation 18 IUPAC names: replace “ic acid” with “yl halide” / “carboxylic acid” with “carbonyl halide” 19 Reactions of acyl chlorides 20 An amide 21 Amide formation 22 IUPAC names: replace “ic acid”, “oic acid”, “ylic acid” with “amide” 23 Reactions of amides 24 Reaction only in the presence of an acid 25 The Hell-Vohard-Zelinski reaction Only for α-hydrogens Radical substitution (halogenation) will occurs in the absence of PBr3, P 26 Reaction mechanism: 27 28 Reduction reactions H2/Ni, Pt, Pd or NaBH4 can NOT reduce acids, esters, amides 29 LiAlH4 is used to reduce only compounds such as acids, esters, amides that can NOT be reduced by milder agents 30