Textbook Question
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(c) cyclohexanecarboxamide
(d)
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Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 21, Problem 10a
Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.
Verified step by step guidance1
Step 1: Understand the reactivity of acetic anhydride. Acetic anhydride is a reactive acylating agent that reacts with alcohols to form esters and with amines to form amides. This is a nucleophilic acyl substitution reaction.
Step 2: For the synthesis of benzyl acetate (i), identify the appropriate alcohol. Benzyl acetate is an ester, so the alcohol required is benzyl alcohol (C₆H₅CH₂OH). The reaction involves the nucleophilic attack of the hydroxyl group (-OH) of benzyl alcohol on the carbonyl carbon of acetic anhydride.
Step 3: Write the reaction for benzyl acetate synthesis. The reaction is: . Here, benzyl alcohol reacts with acetic anhydride to form benzyl acetate and acetic acid as a byproduct.
Step 4: For the synthesis of N,N-diethylacetamide (ii), identify the appropriate amine. N,N-diethylacetamide is an amide, so the amine required is diethylamine (CH₃CH₂)₂NH. The reaction involves the nucleophilic attack of the amine's nitrogen on the carbonyl carbon of acetic anhydride.
Step 5: Write the reaction for N,N-diethylacetamide synthesis. The reaction is: . Here, diethylamine reacts with acetic anhydride to form N,N-diethylacetamide and acetic acid as a byproduct.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetic Anhydride
Acetic anhydride is a reactive organic compound used as an acylating agent in organic synthesis. It can react with alcohols and amines to form esters and amides, respectively, through nucleophilic acyl substitution. Understanding its reactivity and the conditions required for these reactions is crucial for synthesizing compounds like benzyl acetate and N,N-diethylacetamide.
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Anhydride Nomenclature
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of the leaving group. This mechanism is essential for the formation of esters and amides from acylating agents like acetic anhydride and alcohols or amines, respectively.
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Functional Group Transformation
Functional group transformation involves converting one functional group into another, which is a key aspect of organic synthesis. In this context, transforming acetic anhydride into an ester (benzyl acetate) or an amide (N,N-diethylacetamide) requires understanding the properties and reactivity of the starting materials and the desired products, as well as the reaction conditions that favor these transformations.
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Related Practice
Textbook Question
Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.
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Textbook Question
When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for formation of this lactone.
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Textbook Question
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH3)
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Textbook Question
Acid-catalyzed transesterification:
Complete the mechanism for this acid-catalyzed transesterification by drawing out all the individual steps. Draw the important resonance contributors for each resonance-stabilized intermediate.
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Textbook Question
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate