Textbook Question
Predict the products of the following reactions.
(a) phenol + acetic anhydride
(b) phenol + acetic formic anhydride
(c) aniline + phthalic anhydride
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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 44a,b,c
Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.
(a) ethanol
(b) sodium acetate
(c) aniline
Verified step by step guidance1
Step 1: Recognize the functional group in benzoyl chloride (PhCOCl). It contains an acyl chloride group (-COCl), which is highly reactive and undergoes nucleophilic acyl substitution reactions.
Step 2: For reaction (a) with ethanol: Ethanol (CH3CH2OH) acts as a nucleophile. The lone pair on the oxygen atom of ethanol attacks the carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate tetrahedral structure. The chloride ion (Cl⁻) is then eliminated, resulting in the formation of ethyl benzoate (PhCOOCH2CH3).
Step 3: For reaction (b) with sodium acetate: Sodium acetate (CH3COONa) contains the acetate ion (CH3COO⁻), which acts as a nucleophile. The acetate ion attacks the carbonyl carbon of benzoyl chloride, forming an intermediate. The chloride ion (Cl⁻) is displaced, leading to the formation of acetic anhydride (PhCOOCOCH3).
Step 4: For reaction (c) with aniline: Aniline (PhNH2) is a nucleophilic amine. The lone pair on the nitrogen atom of aniline attacks the carbonyl carbon of benzoyl chloride, forming an intermediate. The chloride ion (Cl⁻) is eliminated, resulting in the formation of N-phenylbenzamide (PhCONHPh).
Step 5: Summarize the reactions: (a) Ethanol forms ethyl benzoate, (b) Sodium acetate forms acetic anhydride, and (c) Aniline forms N-phenylbenzamide. These are all examples of nucleophilic acyl substitution reactions.
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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, such as benzoyl chloride, are reactive compounds that contain a carbonyl group (C=O) bonded to a chlorine atom. They are known for their ability to undergo nucleophilic acyl substitution reactions, where the chlorine atom is replaced by a nucleophile. Understanding the reactivity of acyl chlorides is crucial for predicting the products of their reactions with various nucleophiles.
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Recognizing acyl chlorides and anhydrides.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, leading to the replacement of a leaving group. In the case of benzoyl chloride, the nucleophile can be an alcohol, an amine, or a carboxylate ion, each resulting in different products. Recognizing the nature of the nucleophile is essential for predicting the outcome of the reaction.
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Product Formation
The formation of products in organic reactions depends on the nature of the reactants and the reaction conditions. For benzoyl chloride, the products formed when reacting with ethanol, sodium acetate, and aniline will vary based on the nucleophilic character of each reagent. Understanding how to identify and predict these products is key to mastering organic synthesis and reaction mechanisms.
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Related Practice
Textbook Question
Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.
(d) anisole and aluminum chloride
(e) excess phenylmagnesium bromide, then dilute acid
(f) LiAlH(O-t-Bu)3
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Textbook Question
Give appropriate names for the following compounds:
(k)
(l)
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Textbook Question
Give appropriate names for the following compounds:
(g)
(h)
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Textbook Question
Give appropriate names for the following compounds:
(i)
(j)
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Textbook Question
Predict the products of the following reactions.
(d) anisole + succinic anhydride and aluminum chloride
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