23FA262_Lesson_26_Amides_ post-class-8

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Oct 30, 2023

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Amide Reactions: General Scheme Amides are not very electrophilic due to the strong resonance contribution from N Recall: 2 peaks for N-CH 3 ’s of an amide in a 1 H NMR due to the barrier of rotation around the C-N bond Amides are quite stable due to excellent orbital overlap and resonance contribution Reactions with amides require very good nucleophiles and/or strong bases For hydrolysis, an acid catalyst and heat or hydroxide and heat are required Three different reaction perturbations: 1. Negatively charged nucleophile 2. Neutral nucleophile (must be good nuc) 3. Neutral nucleophile with catalytic acid or base and HEAT The strength of the electrophile and nucleophile determines the reaction conditions and mechanism
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