Lecture27outline

Lecture27outline - I. Review Nitriles can be reduced by...

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I. Review • Nitriles can be reduced by DIBAL to form imines that can be hydrolyzed to form aldehydes • LiAlH 4 reduce nitriles to primary amines because the hydride of LiAlH 4 is sufficiently reactive to add to the intermediate from monoaddition • Nitriles undergo hydrogenation in the presence of PtO 2 or other transition metal catalysts to form primary amines under mild conditions • Carboxylic acids and derivatives can be converted to nucleophiles through deprotonation • Carboxylic acid enolates are rare because deprotonation of the O–H group is far more favorable • Carboxylic acids react with diazomethane (CH 2 N 2 ) to form methyl esters through a process in which proton transfer leads to the formation of a carboxylate and CH 3 N 2 + , which undergo a rapid S N 2 reaction to liberate N 2 • The Mitsunobu reaction is a nucleophilic esterification reaction between caboxylic acids, alcohols, diethylazo dicarboxylate (DEAD), and Ph 3 P • This reaction proceeds through the protonation of DEAD by the carboxylic acid,
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Lecture27outline - I. Review Nitriles can be reduced by...

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