Textbook Question
Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.
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 9a,b
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH3)
Verified step by step guidance1
Identify the general reaction for amide synthesis: Amides can be synthesized by reacting an acyl chloride with an amine. The reaction involves nucleophilic acyl substitution, where the amine attacks the carbonyl carbon of the acyl chloride, leading to the formation of the amide and the release of HCl.
For part (a), N,N-dimethylacetamide: Determine the required acyl chloride and amine. The structure of N,N-dimethylacetamide suggests that the acyl chloride should be acetyl chloride (CH3COCl), and the amine should be dimethylamine ((CH3)2NH).
Write the reaction for part (a): Combine acetyl chloride (CH3COCl) with dimethylamine ((CH3)2NH). The reaction proceeds as follows:
For part (b), acetanilide (PhNHCOCH3): Determine the required acyl chloride and amine. The structure of acetanilide suggests that the acyl chloride should again be acetyl chloride (CH3COCl), and the amine should be aniline (PhNH2).
Write the reaction for part (b): Combine acetyl chloride (CH3COCl) with aniline (PhNH2). The reaction proceeds as follows:
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom. They are highly reactive towards nucleophiles, making them useful in organic synthesis, particularly for forming amides. In the context of the question, acyl chlorides can be reacted with amines to produce the desired amides.
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Recognizing acyl chlorides and anhydrides.
Amines
Amines are organic compounds that contain nitrogen atoms bonded to carbon atoms. They can act as nucleophiles due to the lone pair of electrons on the nitrogen, allowing them to react with electrophiles like acyl chlorides. In synthesizing amides, the amine reacts with the acyl chloride to form the amide bond, releasing hydrochloric acid as a byproduct.
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Amide Formation
Amide formation is a key reaction in organic chemistry where an amine reacts with a carboxylic acid derivative, such as an acyl chloride, to produce an amide. This reaction typically involves nucleophilic attack by the amine on the carbonyl carbon of the acyl chloride, leading to the formation of the amide bond (C=O-N). Understanding this mechanism is crucial for synthesizing specific amides like N,N-dimethylacetamide and acetanilide.
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Related Practice
Textbook Question
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(c) cyclohexanecarboxamide
(d)
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Textbook Question
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(c) benzyl benzoate
(d) cyclopropyl cyclohexanecarboxylate
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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
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(a) ethyl propionate
(b) phenyl 3-methylhexanoate
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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