Textbook Question
What are the products of the following reactions?
a.
b.
c.
d.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of 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. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 23b
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 23bChapter 17, Problem 23b
How would you make the following compounds from N-benzylbenzamide?
b. benzoic acid
Verified step by step guidance1
Step 1: Identify the functional groups in N-benzylbenzamide. The molecule contains an amide group (-CONH-) attached to a benzyl group and a benzene ring.
Step 2: Recognize that benzoic acid is the target compound, which contains a carboxylic acid group (-COOH) attached to a benzene ring. This indicates that the amide group must be hydrolyzed to form the carboxylic acid.
Step 3: Plan the reaction. Hydrolysis of the amide group can be achieved using either acidic or basic conditions. For example, you can use aqueous HCl (acidic hydrolysis) or aqueous NaOH (basic hydrolysis) followed by acidification.
Step 4: Perform the hydrolysis. Under acidic conditions, the amide group is protonated, making it more susceptible to nucleophilic attack by water. This leads to the cleavage of the C-N bond, forming benzoic acid and releasing benzylamine as a byproduct.
Step 5: Isolate and purify the benzoic acid. After the reaction is complete, the mixture can be acidified (if basic hydrolysis was used) and the benzoic acid can be extracted and purified using techniques such as recrystallization.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
N-benzylbenzamide Structure
N-benzylbenzamide is an amide compound where a benzyl group is attached to the nitrogen of a benzamide. Understanding its structure is crucial for predicting its reactivity in chemical reactions, particularly in transformations that involve the cleavage of the amide bond or functional group modifications.
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Hydrolysis of Amides
Hydrolysis is a chemical reaction involving the breakdown of a compound by water. In the case of amides, hydrolysis can convert them into carboxylic acids and amines. This reaction is essential for converting N-benzylbenzamide into benzoic acid, as it involves the cleavage of the amide bond and the addition of a hydroxyl group.
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Carboxylic Acid Formation
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). The formation of benzoic acid from N-benzylbenzamide involves the introduction of this functional group through hydrolysis. Understanding the properties and reactivity of carboxylic acids is important for predicting their behavior in further chemical reactions.
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Related Practice
Textbook Question
How would you make the following compounds from N-benzylbenzamide?
a. dibenzylamine
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Textbook Question
What amides would you react with LiAlH4 to form the following amines?
a. benzylmethylamine
b. ethylamine
c. diethylamine
d. triethylamine
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Textbook Question
What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid?
c. methyl benzoate
d. pentanoic acid
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Textbook Question
A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate formed in this reaction, and show how it can be converted to a ketone.
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Textbook Question
How would you make the following compounds from N-benzylbenzamide?
c. benzyl alcohol
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