Textbook Question
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
e. aqueous NaOH
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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 50i
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 50iChapter 16, Problem 50i
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
i. isopropyl alcohol
Verified step by step guidance1
Step 1: Recognize the type of reaction. Benzoyl chloride (C₆H₅COCl) is an acyl chloride, and it reacts with alcohols to form esters in a reaction known as the Fischer esterification or nucleophilic acyl substitution.
Step 2: Identify the nucleophile. In this case, isopropyl alcohol (CH₃CHOHCH₃) acts as the nucleophile, where the hydroxyl (-OH) group will attack the carbonyl carbon of benzoyl chloride.
Step 3: Describe the mechanism. The lone pair of electrons on the oxygen atom of isopropyl alcohol attacks the electrophilic carbonyl carbon of benzoyl chloride, forming a tetrahedral intermediate. Simultaneously, the chlorine atom (Cl⁻) is displaced as a leaving group.
Step 4: Proton transfer. A proton (H⁺) is transferred from the oxygen of the isopropyl alcohol to the chlorine atom, forming HCl as a byproduct.
Step 5: Write the product. The final product is isopropyl benzoate (C₆H₅COOCH(CH₃)₂), an ester, along with HCl as a byproduct.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Benzoyl Chloride
Benzoyl chloride is an acyl chloride derived from benzoic acid. It is a reactive compound that can undergo nucleophilic acyl substitution reactions, where the chlorine atom is replaced by a nucleophile. Understanding its reactivity is crucial for predicting the products formed when it reacts with alcohols or other nucleophiles.
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Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the replacement of a leaving group. In the case of benzoyl chloride reacting with isopropyl alcohol, the alcohol acts as the nucleophile, resulting in the formation of an ester.
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Ester Formation
Ester formation occurs when a carboxylic acid or an acyl chloride reacts with an alcohol, resulting in the production of an ester and the release of a molecule of hydrochloric acid (HCl in the case of acyl chlorides). The reaction between benzoyl chloride and isopropyl alcohol specifically yields isopropyl benzoate, an important ester used in various applications.
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Related Practice
Textbook Question
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
k. potassium formate
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Textbook Question
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
g. excess benzylamine
h. 4-chlorophenol
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Textbook Question
What compounds are obtained from the following hydrolysis reactions?
d.
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Textbook Question
What compounds are obtained from the following hydrolysis reactions?
c.
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Textbook Question
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
f. cyclohexanol
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