Tài liệu Bài giảng organic chemistry chapter11

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: [email protected] 1 Chapter 11: C=O ALDEHYDES-KETONES C=C SP2 carbon 2 NOMENCLATURE OF ALDEHYDES “aldehyde” Common names: carboxylic acid is substituted for “ic acid” IUPAC names: hydrocarbon + al 3 Lower priority than ester “oxo” group 4 5 NOMENCLATURE OF KETONES Derived names: alkyls + ketone IUPAC names: hydrocarbon + one 6 7 PREPARATION OF ALDEHYDES & KETONES Aldehydes & ketones from alkenes In the presence of an oxidizing agent, the products 8 will be ketones / carboxylic acids Aldehydes & ketones from alkynes Markovnikov’s rule Anti-Markovnikov 9 Aldehydes & ketones from alcohols 10 Can NOT be isolated PCC: pyridinium chlorochromate 11 Aldehydes from esters, acyl chlorides Note: LiAlH4 alcohols 12 Preparation of aromatic ketones 13 Gatterman-Koch synthesis of benzaldehyde Can NOT be prepared & isolated 14 REACTIONS OF ALDEHYDES & KETONES I The partial positive carbon can be attacked by nucleophiles The addition of nucleophiles to the carbon atom of the carbonyl group in nucleophilic addition reactions 15 Reactions with Grignard reagents Only for the reaction of HCHO 16 Numbers 1 & 2 are used to indicate that the acid is not added until the reaction with the Grignard reagent is complete 17 Reactions with acetylide ions Weak acid, will NOT react with the triple bond 18 Reactions with hydrogen cyanide Converted back to carbonyl in basic solutions 19 Nitriles Nitriles carboxylic acids amines 20