lecture 16.4

lecture 16.4 - 16-16-1Organic Organic H BrownWilliam H...

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Unformatted text preview: 16-16-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson16-16-2Aldehydes Aldehydes & & KetonesKetonesChapter 16Chapter 1616-16-3Oxidation of AldehydesOxidation of Aldehydes◆Aldehydes are oxidized to carboxylic acids by a variety of oxidizing agents, including H2CrO4◆They are also oxidized by Ag(I) •in one method, a solution of the aldehyde in aqueous ethanol or THF is shaken with a slurry of silver oxide CHOH2CrO4COOHHexanalHexanoic acidVanillic acidVanillin++CHHOCH3OOOCH3OHOCOHAg2OTHF, H2ONaOHAgHClH2O16-16-4Oxidation of AldehydesOxidation of Aldehydes◆Aldehydes are oxidized by O2in a radical chain reaction•liquid aldehydes are so sensitive to air that they must be stored under N2Benzoic acidBenzaldehyde+CHOOCOH2O2216-16-5Oxidation of KetonesOxidation of Ketones•ketones are not normally oxidized by chromic acid•they are oxidized by powerful oxidants at high temperature and high concentrations of acid or baseH exanedioic acid(Adipic acid)Cyclohexanone(keto form)Cyclohexanone(enol form)HNO3OHOOHOOOH16-16-6ReductionReduction•aldehydes can be reduced to 1° alcohols•ketones can be reduced to 2° alcohols •the C=O group of an aldehyde or ketone can be reduced to a -CH2- groupAldehydesCan BeReduced toKetonesCan BeReduced toOOOHRCHRCH2OHRCH3RCR'RCHR'RCH2R'16-16-7Metal Hydride ReductionMetal Hydride Reduction◆The most common laboratory reagents for the...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 16.4 - 16-16-1Organic Organic H BrownWilliam H...

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