Textbook Question
Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?
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 8a,b
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(a) ethyl propionate
(b) phenyl 3-methylhexanoate
Verified step by step guidance1
Identify the ester structure and break it down into its two components: the alcohol and the acyl chloride. For an ester, the part attached to the oxygen (R-O) comes from the alcohol, and the part attached to the carbonyl group (R-C=O) comes from the acyl chloride.
For (a) ethyl propionate: The ester is composed of an ethyl group (from ethanol, CH₃CH₂OH) and a propionyl group (from propionyl chloride, CH₃CH₂COCl).
For (b) phenyl 3-methylhexanoate: The ester is composed of a phenyl group (from phenol, C₆H₅OH) and a 3-methylhexanoyl group (from 3-methylhexanoyl chloride, CH₃CH₂CH(CH₃)CH₂CH₂COCl).
Write the general reaction for esterification: An acyl chloride reacts with an alcohol to form an ester and HCl. The reaction can be represented as: .
Combine the appropriate alcohol and acyl chloride for each ester: (a) React ethanol (CH₃CH₂OH) with propionyl chloride (CH₃CH₂COCl) to form ethyl propionate. (b) React phenol (C₆H₅OH) with 3-methylhexanoyl chloride (CH₃CH₂CH(CH₃)CH₂CH₂COCl) to form phenyl 3-methylhexanoate.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Esterification Reaction
Esterification is a chemical reaction between an alcohol and a carboxylic acid (or acyl chloride) that produces an ester and water. In this process, the hydroxyl group of the acid reacts with the hydrogen of the alcohol, leading to the formation of an ester bond. Understanding this reaction is crucial for synthesizing esters, as it outlines the fundamental mechanism involved.
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Reactions of Amino Acids: Esterification Concept 1
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are reactive derivatives of carboxylic acids where the hydroxyl group is replaced by a chlorine atom. They are highly reactive and can readily react with alcohols to form esters. Recognizing the role of acyl chlorides in ester synthesis is essential, as they provide a more efficient pathway compared to using carboxylic acids directly.
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Guided course
01:57Recognizing acyl chlorides and anhydrides.
Alcohols in Ester Synthesis
Alcohols are organic compounds containing one or more hydroxyl (-OH) groups. In ester synthesis, the choice of alcohol affects the structure and properties of the resulting ester. For example, using ethanol will yield ethyl esters, while using phenol will yield phenyl esters. Understanding the specific alcohols needed for the desired esters is key to successful synthesis.
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Related Practice
Textbook Question
Which of the following proposed reactions would take place quickly under mild conditions?
(a)
(b)
(c)
(d)
(e)
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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 aniline with acetic anhydride to give acetanilide.
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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
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate