Chapter 12: CARBOXYLIC ACIDS doc

1 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@hcmut.edu.vn 2 Chapter 12: CARBOXYLIC ACIDS C=O C=C SP 2 carbon Y=OH 3 NOMENCLATURE OF CARBOXYLIC ACIDS IUPAC names: hydrocarbon + “oic acid” 4 5 6 Some natural occurring acids & derivatives 7 PREPARATIONS OF CARBOXYLIC ACIDS From Grignard reagents 8 From nitriles Have 1 more carbon as compared to the halide 9 From primary alcohols Can NOT be isolated PCC: pyridinium chlorochromate 10 From aldehydes Aldehydes are generally easier to oxidize than primary alcohols [...]...From alkylbenzenes 11 REACTIONS OF CARBOXYLIC ACIDS Esterification reactions 12 IUPAC names: alkyl + carboxylate 13 Intramolecular ester formation: Lactones 14 IUPAC names: 2-oxacycloalkanone 15 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... -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 . ptsnam@hcmut.edu.vn 2 Chapter 12: CARBOXYLIC ACIDS C=O C=C SP 2 carbon Y=OH 3 NOMENCLATURE OF CARBOXYLIC ACIDS IUPAC names: hydrocarbon + “oic acid” 4 5 6 Some natural occurring acids & derivatives . hydrocarbon + “oic acid” 4 5 6 Some natural occurring acids & derivatives 7 PREPARATIONS OF CARBOXYLIC ACIDS From Grignard reagents 8 From nitriles Have 1 more carbon as compared to the halide . generally easier to oxidize than primary alcohols 11 From alkylbenzenes 12 REACTIONS OF CARBOXYLIC ACIDS Esterification reactions 13 IUPAC names: alkyl + carboxylate 14 Intramolecular ester