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Lecture26outline - I Review Secondary amides do not show...

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I. Review • Secondary amides do not show multiple signals in the 1 H NMR because of the strong thermodynamic preference for the alkyl groups to have a trans -relationship • Amides are the most stable carboxylic acid derivatives, making them suitable for linkages between amino acids in proteins • Amides have been shown to have a half-life of approximately 7 years at room temperature and neutral pH through a clever experiment that utilized polymer immobilization and kinetic analysis by determining radioactivity increases as a function of time • Amides can be hydrolyzed to carboxylic acids using either acid or base, but high temperatures are required • Tertiary amides react with DIBAL to yield aldehydes because of the stable tetrahedral intermediate that arises from the poor leaving group • Amides react with LiAlH 4 to yield amines because the oxygen, coordinated to both Al and Li, leaves in preference to the nitrogen when the tetrahedral intermediate collapses,
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