Textbook Question
Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.
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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 6d
Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.
Verified step by step guidance1
Step 1: Identify the reactants and the product. The reactants are aniline (C6H5NH2) and acetic anhydride ((CH3CO)2O), and the product is acetanilide (C6H5NHCOCH3). This reaction involves the acetylation of aniline.
Step 2: Recognize the nucleophilic site on aniline. The nitrogen atom in aniline has a lone pair of electrons, making it nucleophilic and capable of attacking the electrophilic carbonyl carbon in acetic anhydride.
Step 3: Initiate the reaction mechanism. The lone pair of electrons on the nitrogen atom of aniline attacks one of the carbonyl carbons in acetic anhydride, forming a tetrahedral intermediate. This step involves nucleophilic addition.
Step 4: Eliminate the leaving group. The tetrahedral intermediate collapses, expelling the acetate ion (CH3COO−) as a leaving group. This step results in the formation of the amide bond between the nitrogen of aniline and the acetyl group.
Step 5: Finalize the product. The reaction yields acetanilide (C6H5NHCOCH3) as the final product, with acetate ion as a byproduct. This is an example of an acylation reaction where aniline is converted into an amide.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbonyl carbon, leading to the substitution of a leaving group. In the case of aniline reacting with acetic anhydride, the amino group of aniline acts as the nucleophile, attacking the carbonyl carbon of the acetic anhydride, resulting in the formation of acetanilide.
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01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.
Role of Acetic Anhydride
Acetic anhydride is a reactive acylating agent commonly used in organic synthesis. It provides an acyl group (CH3CO-) that can be transferred to nucleophiles. In this reaction, acetic anhydride not only serves as the source of the acyl group but also facilitates the formation of the amide bond in acetanilide by releasing acetic acid as a byproduct.
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03:35Anhydride Nomenclature
Amide Formation
Amide formation is a key reaction in organic chemistry where a carboxylic acid or its derivative reacts with an amine to form an amide. In this case, the reaction between aniline and acetic anhydride results in the formation of acetanilide, an amide, through the nucleophilic attack of the aniline nitrogen on the carbonyl carbon of the acetic anhydride, followed by the elimination of acetic acid.
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Related Practice
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?
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.
(a) ethyl propionate
(b) phenyl 3-methylhexanoate
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Textbook Question
Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.
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Textbook Question
Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.
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