Chem 239 C: Chapter 19 Carboxylic Acid Derivatives Goals: Description, Nomenclature Reactivity of Carboxylic Acid Derivatives Nucleophylic Acyl
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1 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives Goals: Description, Nomenclature Reactivity of Carboxylic Acid Derivatives Nucleophylic Acyl Substitution Acyl Chlorides Carboxylic Acid Anhydrides, Esters Mechanisms of ester hydrolysis Amides, Lactams, Imides, and Nitriles Mechanisms of amide hydrolysis Reading: 9 th Ed: Pg , 19.2, 19.3, 19.4, 19.5, 19.7, 19.8, 19.9, 19.10, 19.11, 19.12, 19.13, 19.14, 19.15,
2 Chapter 19: Reading Priorities (9 th Edition) I don t want to be an unemployable chemist 19.1, 19.2, 19.3, 19.4, 19.5, 19.7, 19.8, 19.9, 19.10, 19.12, I want to be the best doctor All on the left, plus 19.11, 19.14, 19.15, I want Professor Rathod s job! All on the left, plus 19.16, 19.17, Text book Chapter 19: Practice problems (9 th Edition) 19.27, ,19.43, 19.44, More online practice on Sapling Learning Graded Homework on Sapling Homework Ch 19 Not timed. Multiple opportunities up to the due date.
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5 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives Goals: Description, Nomenclature Reactivity of Carboxylic Acid Derivatives Nucleophylic Acyl Substitution Acyl Chlorides Carboxylic Acid Anhydrides, Esters Mechanisms of ester hydrolysis Amides, Lactams, Imides, and Nitriles Mechanisms of amide hydrolysis Reading: 9 th Ed: Pg th Ed: Pg th Ed: Pg
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10 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives A different look: Description, Nomenclature Nucleophylic Acyl Substitution Reactivity of Carboxylic Acid Derivatives Hierarchies: e.g. Acyl Chlorides, Acid Anhydrides, Esters Details: e.g. Mechanisms of ester hydrolysis e.g. Mechanisms of amide hydrolysis Looking forward: e.g. Amides, Lactams
11 Examples of Nucleophylic Acyl Substitution reactions
12 Arriving at a tetrahedral intermediate
13 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives A different look: Description, Nomenclature Nucleophylic Acyl Substitution Reactivity of Carboxylic Acid Derivatives Hierarchies: e.g. Acyl Chlorides, Acid Anhydrides, Esters Details: e.g. Mechanisms of ester hydrolysis e.g. Mechanisms of amide hydrolysis Looking forward: e.g. Amides, Lactams
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15 O RCCl O O RCOCR' O RCOR' O RCNR' 2 Stabilization? very small small moderate large Relative rate of hydrolysis < 10-2
16 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives A different look: Description, Nomenclature Nucleophylic Acyl Substitution Reactivity of Carboxylic Acid Derivatives Hierarchies: e.g. Acyl Chlorides, Acid Anhydrides, Esters Details: e.g. Mechanisms of ester hydrolysis e.g. Mechanisms of amide hydrolysis Looking forward: e.g. Amides, Lactams
17 Most reactive Least reactive
18 Mid-reactive
19 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives A different look: Description, Nomenclature Nucleophylic Acyl Substitution Reactivity of Carboxylic Acid Derivatives Hierarchies: e.g. Acyl Chlorides, Acid Anhydrides, Esters Details: Mech of ester hydrolysis (Mechanism 19.2, 19.3) Mech of amide hydrolysis (Mechanism 19.4, 19.5) Looking forward: e.g. Amides, Lactams
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26 Chem 239B: Chapter 19 Carboxylic Acid Derivatives A different look: Description, Nomenclature Nucleophylic Acyl Substitution Reactivity of Carboxylic Acid Derivatives Hierarchies: e.g. Acyl Chlorides, Acid Anhydrides, Esters Details: e.g. Mechanisms of ester hydrolysis e.g. Mechanisms of amide hydrolysis Looking forward : Amides, Lactams
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28 Energetics: Chemical solution
29 Energetics: Biological solution
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32 Norman Heatley
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34 CHEM 239 RATHOD 2017 FINAL EXAM: Things to know CARBOXYLIC ACID DERIVATIVES MAJOR CLASSES Acyl chlorides, anhydrides, thioesters, esters, amides, nitriles Relative reactivities of the above ACYL TRANSFER REACTIONS Know mechanisms, intermediates Acid vs Base catalysis IMPORTANT DERIVATIVES Amides, lactams, Nitriles
35 Chem 239 C: Chapter 19 Carboxylic Acid Derivatives Goals: Description, Nomenclature Reactivity of Carboxylic Acid Derivatives Nucleophylic Acyl Substitution Acyl Chlorides Carboxylic Acid Anhydrides, Esters Mechanisms of ester hydrolysis Amides, Lactams, Imides, and Nitriles Mechanisms of amide hydrolysis Reading: 9 th Ed: Pg th Ed: Pg th Ed: Pg
Carboxylic Acid Derivatives Reading Study Problems Key Concepts and Skills Lecture Topics: Structures and reactivity of carboxylic acid derivatives
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CARBOXYLIC ACIDS AND THEIR DERIVATIVES: NUCLEOPHILIC ADDITION-ELIMINATION AT THE ACYL CARBON
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