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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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 50k
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 50kChapter 16, Problem 50k
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
k. potassium formate
Verified step by step guidance1
Step 1: Recognize the functional group in benzoyl chloride. Benzoyl chloride contains an acyl chloride functional group (-COCl) attached to a benzene ring. Acyl chlorides are highly reactive and can undergo nucleophilic acyl substitution reactions.
Step 2: Identify the reagent, potassium formate (HCOOK). Potassium formate is the potassium salt of formic acid (HCOOH) and acts as a nucleophile due to the presence of the formate ion (HCOO⁻).
Step 3: Understand the reaction mechanism. In the presence of potassium formate, the nucleophilic formate ion (HCOO⁻) attacks the carbonyl carbon of the benzoyl chloride. This is a nucleophilic acyl substitution reaction, where the chloride ion (Cl⁻) is displaced as the leaving group.
Step 4: Predict the product. The substitution of the chloride ion by the formate ion results in the formation of benzoyl formate (C₆H₅COOCHO), which is an ester. The byproduct of the reaction is potassium chloride (KCl).
Step 5: Summarize the reaction. The overall reaction can be written as: C₆H₅COCl + HCOOK → C₆H₅COOCHO + KCl. This shows the formation of benzoyl formate and potassium chloride as the products.
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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. In these reactions, the chlorine atom is replaced by a nucleophile, leading to the formation of various products depending on the nucleophile used.
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Acid Chloride Nomenclature
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 (like chloride) with the nucleophile. This reaction is crucial for understanding how different reagents interact with acyl chlorides, resulting in diverse organic compounds.
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Potassium Formate
Potassium formate is the potassium salt of formic acid and acts as a nucleophile in organic reactions. When it reacts with benzoyl chloride, the formate ion can attack the carbonyl carbon, leading to the formation of benzoyl formate. This reaction exemplifies how carboxylate ions can participate in nucleophilic acyl substitution.
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Related Practice
Textbook Question
Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.
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Textbook Question
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
i. isopropyl alcohol
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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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