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 8e,f
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate
Verified step by step guidance1
Identify the esterification reaction: Esters are typically synthesized via a reaction between an acyl chloride and an alcohol in the presence of a base (e.g., pyridine) to neutralize the HCl byproduct.
For tert-butyl acetate: Recognize that the ester is composed of the tert-butyl group (from tert-butyl alcohol) and the acetate group (from acetic acid or its derivative). The acyl chloride needed is acetyl chloride (CH₃COCl), and the alcohol is tert-butyl alcohol ((CH₃)₃COH).
Write the reaction for tert-butyl acetate synthesis: Combine acetyl chloride (CH₃COCl) with tert-butyl alcohol ((CH₃)₃COH) in the presence of a base like pyridine. The reaction proceeds as follows: .
For diallyl succinate: Recognize that the ester is derived from succinic acid (or its derivative) and allyl alcohol. The acyl chloride needed is succinyl chloride (ClCO(CH₂)₂COCl), and the alcohol is allyl alcohol (CH₂=CHCH₂OH).
Write the reaction for diallyl succinate synthesis: Combine succinyl chloride (ClCO(CH₂)₂COCl) with two equivalents of allyl alcohol (CH₂=CHCH₂OH) in the presence of a base like pyridine. 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 and serve as key intermediates in organic synthesis, particularly in the formation of esters and amides. Their reactivity allows them to easily react with alcohols to form esters through nucleophilic acyl substitution.
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Recognizing acyl chlorides and anhydrides.
Esterification Reaction
Esterification is a chemical reaction that forms an ester from an alcohol and an acid (or acyl chloride). In this process, the hydroxyl group of the acid and a hydrogen atom from the alcohol are eliminated, resulting in the formation of an ester and water. This reaction is typically catalyzed by an acid and is crucial for synthesizing various esters, including those mentioned in the question.
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1:21Reactions of Amino Acids: Esterification Concept 1
Synthesis of Diallyl Succinate
Diallyl succinate is a diester formed from succinic acid and allyl alcohol. The synthesis involves the reaction of succinic acid's acyl chloride with two equivalents of allyl alcohol, leading to the formation of the diester. Understanding the structure of succinic acid and the reactivity of allyl alcohol is essential for successfully synthesizing this compound through esterification.
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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
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
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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