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Chapter 21 Carboxylic Acid Derivatives

Chapter 21 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution Reactions. 2 steps in reaction Formation of tetrahedral intermediate Collapse of tetrahedral intermediate. The weaker the base ( Y ) attached to the acyl group, the easier It is for both steps of the reaction.

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Chapter 21 Carboxylic Acid Derivatives

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  1. Chapter 21Carboxylic Acid Derivatives

  2. Nucleophilic Acyl Substitution Reactions • 2 steps in reaction • Formation of tetrahedral intermediate • Collapse of tetrahedral intermediate The weaker the base (Y) attached to the acyl group, the easier It is for both steps of the reaction.

  3. Reactivity of Nucleophilic Acyl Substitution Reactions Reactivity: > > > Basicity: < < <

  4. The weaker the base (Y) attached to the acyl group, the easier it is for both steps of the reaction. • 2 steps in reaction • Formation of tetrahedral intermediate -the less basic substituent is more electronegative, drawing electron density away from carbonyl making carbonyl a better electrophile 2. Collapse of tetrahedral intermediate - less basic substituent has a weaker bond (easier to break) and is happier carrying negative charge as expelled anion

  5. Carboxylic Acid Derivatives:Synthesis from Carboxylic Acid

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