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 8c,d
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(c) benzyl benzoate
(d) cyclopropyl cyclohexanecarboxylate
Verified step by step guidance1
Identify the ester structure and break it down into its two components: the alcohol and the acyl chloride. For benzyl benzoate, the ester is derived from benzyl alcohol (C₆H₅CH₂OH) and benzoyl chloride (C₆H₅COCl). For cyclopropyl cyclohexanecarboxylate, the ester is derived from cyclopropanol (C₃H₅OH) and cyclohexanecarbonyl chloride (C₆H₁₁COCl).
Write the general reaction for ester formation: an alcohol reacts with an acyl chloride in the presence of a base (e.g., pyridine or triethylamine) to neutralize the HCl byproduct. The reaction can be represented as: .
For benzyl benzoate: Combine benzyl alcohol (C₆H₅CH₂OH) with benzoyl chloride (C₆H₅COCl) in the presence of a base like pyridine. The base will neutralize the HCl formed during the reaction, driving the reaction to completion.
For cyclopropyl cyclohexanecarboxylate: Combine cyclopropanol (C₃H₅OH) with cyclohexanecarbonyl chloride (C₆H₁₁COCl) in the presence of a base like pyridine. Again, the base will neutralize the HCl byproduct, ensuring the reaction proceeds efficiently.
Ensure proper reaction conditions: Use an anhydrous solvent (e.g., dichloromethane) to prevent hydrolysis of the acyl chloride, and maintain a controlled temperature to avoid side reactions. After the reaction, purify the ester product using techniques like extraction and distillation.
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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 an acyl chloride (or carboxylic acid) that produces an ester and hydrochloric acid. This reaction typically occurs under mild conditions and is characterized by the nucleophilic attack of the alcohol's hydroxyl group on the carbonyl carbon of the acyl chloride, leading to the formation of the ester bond.
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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 serve as excellent electrophiles in nucleophilic acyl substitution reactions, making them ideal starting materials for synthesizing esters when reacted with alcohols.
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01:57Recognizing acyl chlorides and anhydrides.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of ester synthesis, the alcohol acts as the nucleophile, attacking the carbonyl carbon of the acyl chloride, which leads to the formation of the ester and the release of a chloride ion.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
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
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 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.
(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