Chapter 21 Templates - Chapter 21: Carboxylic Acid...

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Unformatted text preview: Chapter 21: Carboxylic Acid Derivatives and Nucleophilic Acyl Substitutions Reactions General Overview of Carboxylic Compounds: Y Group = Carboxylic Acid Acid Halide (Cl and Br only) Acid Anhydride Ester Amide Thioester Acyl Phosphate Structure: acyl group bonded to "Y" (an electronegative atom/group) Halide, acyloxy, alkoxy, amine, thiolate, phosphate Title: Page %d of %d General Reaction Pattern: Nucleophilic Acyl Substitution General Reaction Mechanism: Title: Page %d of %d Nomenclature of Carboxylic Acid Derivatives: 1. Acid Halides: Examples: Replace the "ic acid" ending from the the carboxylic name with "yl" or replace the "carboxylic acid" ending with "carbonyl" and then specify the halide Title: Page %d of %d Nomenclature of Carboxylic Acid Derivatives (cont'd): 2. Acid Anhydrides: Examples: From unsubstituted monocarboxylic acids and symmetrical: replace "acid" with "anhydride" based on the carboxylic acid name From substituted monocarboxylic acids and symmetrical : use the prefix "bis" in front of the acid name rather than "di" If unsymmetrical: list the two acids alphabetically and then replace "acid" with "anhydride" Title: Page %d of %d Nomenclature of Carboxylic Acid Derivatives (cont'd): 3. Amides: Examples: Unsubstituted NH2 group: replace "oic acid" or "ic acid" with "amide" or replace "carboxylic acid" with "carboxamide" If the nitrogen is substituted: identify the substituents (use "N" as a locator) and then add the parent amide name Title: Page %d of %d Nomenclature of Carboxylic Acid Derivatives (cont'd): 4. Esters: Examples: Name R' first then add a space followed by the carboxylic acid name with the " ic acid" ending replaced by "ate" Title: Page %d of %d Summary Table: Title: Page %d of %d Relative Reactivity of Carboxylic Acid Derivatives Nucleophiles react more readily with unhindered carbonyl groups: More electrophilic carbonyl groups are more reactive to addition (to form tetrahedral intermediates) The intermediate with the best leaving group forms the substitution product faster Title: Page %d of %d Consequences of Differing Reactivity on Synthesis:...
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Chapter 21 Templates - Chapter 21: Carboxylic Acid...

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