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Chapter 15_06
Course: CHEM 2300, Fall 2008School: Utah State
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15. Chapter Functional Derivatives of Carboxylic Acids Learning objectives: 1. Recognize the names and structures for the following functional groups: acid halide, acid anhydride, ester, amide, lactone, and lactam. 2. Write the general electron-pushing (arrow-pushing) mechanisms for the nucleophilic acyl substitution of acid halide, acid anhydride, ester, and amide. 3. Explain the order of reactivity toward...
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15. Chapter Functional Derivatives of Carboxylic Acids Learning objectives: 1. Recognize the names and structures for the following functional groups: acid halide, acid anhydride, ester, amide, lactone, and lactam. 2. Write the general electron-pushing (arrow-pushing) mechanisms for the nucleophilic acyl substitution of acid halide, acid anhydride, ester, and amide. 3. Explain the order of reactivity toward nucleophilic acyl substitution among acid halide, acid anhydride, ester, and amide based on the pKa of the conjugate acid of the leaving groups on these four acid derivatives. 4. Provide appropriate reagents and reaction conditions for the feasible interconversions among acid halide, acid anhydride, carboxylic acid, ester, and amide. Sections to be covered (in the order of delivery): 15.1 15.2 15.3 15.4 15.5 15.6 15.7 15.8 15.9 Introduction# Structure and Nomenclature Characteristic Reactions* Reaction with Water Hydrolysis* Reaction with Alcohols* Reaction with Ammonia and Amines* Interconversion of Functional Derivatives* Esters with Grignard Reagents* Reduction
* Sections that will be focused # Sections that will be skipped
Recommended additional problems 15.8 15.43
1
15.2
Structure and Nomenclature
A. Ethanoyl Chloride (Acyl Halides)
B. Acid Anhydrides
C. Esters and Lactones
D. Amides and Lactams
2
15.3
Characteristic Reactions
A. General Reaction
O O R LG (Y) Nu R Nu (Z) O
R
LG
tetrahedral ( intermediate
Nu Z) LG ( Y)
B. Relative Reactivities of Carboxylic Acid Derivatives
O O O O O O
R
Cl
R
O acid anhydride
R
R ester
OR'
R
OH
R amide
NHR'
acyl chloride
carboxylic acid
(i) Inductive effect vs. resonance effect
3
(ii) Nucleophilicity, basicity, and pKa
15.4
Reaction with Water Hydrolysis
A. Acid Chlorides (Acyl Chlorides)
B. Acid Anhydrides
4
C. Esters (i) In Acidic Condition
(i) In Basic Condition
5
D. Amides
15.5
Reaction with Alcohols
A. Acid Chlorides (Acyl Chlorides)
B. Acid Anhydrides
6
C. Esters
D. Amides
15.6
Reaction with Ammonia and Amines
A. Acid Chlorides (Acyl Chlorides)
7
B. Acid Anhydrides
C. Esters
D. Amides
15.7
Interconversion of Functional Derivatives Important Transformation: RCO2H RCOCl Important Reactivity Tendency:
O O O O O
R
Cl
R
O aci...
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2320
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Utah State - CHEM - 2300
Utah State - CHEM - 2300
Utah State - CHEM - 2300