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 23c
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 23cChapter 17, Problem 23c
How would you make the following compounds from N-benzylbenzamide?
c. benzyl alcohol
Verified step by step guidance1
Step 1: Analyze the starting material, N-benzylbenzamide. It contains an amide functional group (-CONH-) attached to a benzyl group and a benzene ring. The target compound, benzyl alcohol, has a hydroxyl (-OH) group attached to the benzyl group.
Step 2: Recognize that the transformation involves breaking the amide bond and reducing the benzyl group to form benzyl alcohol. This requires cleaving the bond between the carbonyl carbon and the nitrogen atom.
Step 3: Use hydrolysis to break the amide bond. Acidic or basic hydrolysis can be employed to convert the amide into a carboxylic acid and a free amine. For example, using HCl or NaOH under heat will yield benzoic acid and benzylamine.
Step 4: Reduce the benzylamine to benzyl alcohol. This can be achieved using a reducing agent such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4), which will convert the amine group (-NH2) to a hydroxyl group (-OH).
Step 5: Purify the benzyl alcohol product using techniques such as distillation or recrystallization, depending on the reaction conditions and the presence of impurities.
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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 recognizing how it can be transformed into other compounds, such as benzyl alcohol. The presence of the amide functional group influences the reactivity and the types of reactions that can be performed on this molecule.
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Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In the context of converting N-benzylbenzamide to benzyl alcohol, a common method is the reduction of the amide group. This process typically requires a reducing agent, such as lithium aluminum hydride (LiAlH4), which effectively converts the carbonyl group of the amide to an alcohol.
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Functional Group Transformation
Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In this case, the transformation of the amide functional group in N-benzylbenzamide to the alcohol functional group in benzyl alcohol is a key step. Understanding how to manipulate functional groups is essential for synthesizing desired organic compounds.
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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
Why is the pKa value of protonated hydroxylamine (6.0) so much lower than the value of a protonated primary amine such as protonated methylamine (10.7)?
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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?
b. benzoic acid
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