lecture 17.2

lecture 17.2 - 17-17-1Organic Organic...

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Unformatted text preview: 17-17-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson17-17-2Carboxylic Carboxylic AcidsAcidsChapter 17Chapter 1717-17-3ReductionReductionThe carboxyl group is very resistant to reductionit is not affected by catalytic hydrogenation under conditions that easily reduce aldehydes and ketones to alcohols, and reduce alkenes and alkynes to alkanes; it is not reduced by NaBH4Lithium aluminum hydride reduces a carboxyl group to a 1 alcohol reduction is carried out in diethyl ether, THF, or other nonreactive, aprotic solventCOHO1. LiAlH42. H2OCH2OHLiOHAl(OH)3++4-Hydroxymethyl- cyclopentene17-17-4Selective ReductionSelective Reductioncarboxyl groups are not affected by catalytic reduction under conditions that reduce aldehydes and ketonesnor are carboxyl groups reduced by NaBH4OHOOH2PtOHOOH5-Hydroxyhexanoic acid(racemic)5-Oxohexanoic acid25 C, 2 atm+C6H5OHOO1. NaBH42. H2OC6H5OHOOH5-Oxo-5-phenylpentanoic acid5-Hydroxy-5-phenylpentanoic acid(racemic)17-17-5Fischer EsterificationFischer EsterificationEsters can be prepared by treating a carboxylic acid with an alcohol in the presence of an acid catalyst, commonly H2SO4, ArSO3H, or gaseous HClEthyl ethanoate(Ethyl acetate)Ethanol(Ethyl alcohol)Ethanoic acid(Acetic acid)++H2SO4H2OOHOHOOO17-17-6Fischer EsterificationFischer Esterification...
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lecture 17.2 - 17-17-1Organic Organic...

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