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CHMB42H3 (16)
Chapter 19

CHMB42 Chapter 19.doc

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Chapter 19 More About OxidationReduction ReactionsFundamentalsRedox Reactions organic reactions that involve the transfer of electrons from one molecule to anotherLEO loss of electrons is oxidationGER gain of electrons is reductionOxidation is always coupled with reduction a species cannot gain electrons unless another species in the reaction simultaneously loses electronsReducing Agent the species that is oxidized because it loses the electrons that are used to reduce the other speciesOxidizing Agent the species that is reduced because it gains the electrons given up by the other species when it is oxidizedReduction at carbon increases the number of CH bonds or decreases the number of CO CN or CX bondsOxidation at carbon decreases the number of CH bonds or increases the number of CO CN or CX bondsReduction ReactionsCatalytic Hydrogenations reduction reactions because there are more CH bonds in the products than in the reactants hydrogen can be added to carboncarbon double and triple bonds in presence of a metal catalyst H and 2PtPdNioAn alkyne can be stopped at a cis alkene if a partially deactivated catalyst is used Lindlar catalystoIt can also be used to reduce carbonnitrogen double and triple bonds to produce aminesoThe carbonyl group of ketones and aldehydes can be reduced by catalytic hydrogenation with Raney nickel as the metal catalyst H and 2Raney nickeloRosenmund Reaction reduction of an acyl chloride can be stopped at an aldehyde if a partially deactivated catalyst is used H and partially 2deactivated PdoCarboxylic acids esters and amides are less reactive than aldehydes and ketones so they cannot be reduced by catalytic hydrogenationDissolvingMetal Reaction when a compound is reduced using sodium in liquid ammonia sodium donates an electron to the compound and ammonia donates a proton overall reaction adds two electrons and two protons to the compoundoAn alkyne can be stopped at a trans alkene using Na or Li with NH liq3oThis cannot reduce a carboncarbon double bond only triple bondsMetalHydride Reductions carbonyl groups are easily reduced by metal hydrides NaBH or LiAlH44oAldehydes ketones and acyl halides can be reduced to alcohols by sodium borohydride NaBH4oLithium aluminum hydride is a stronger reducing agent and also reduces carboxylic acids esters and amides making two compounds0oIf DIBALH is used as a hydride donor at low temperature 78C the reduction of the ester can be stopped after the addition of one equivalent of hydride ionoThe carbonyl group of an amide is reduced to a methylene group CH 2by lithium aluminum hydride
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