Textbook Question
What are the products of the following reactions?
g.
h.
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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 68i,j
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 68i,jChapter 16, Problem 68i,j
What are the products of the following reactions?
i. 
j. 
Verified step by step guidance1
Step 1: Analyze the reaction in part (i). The starting material is an ester (methyl benzoate), and the reagent is excess ammonia (NH₃). Ammonia reacts with esters in a nucleophilic acyl substitution reaction, where the ammonia attacks the carbonyl carbon of the ester.
Step 2: In part (i), the nucleophilic attack by ammonia leads to the formation of an intermediate tetrahedral structure. The methoxy group (-OCH₃) is displaced, resulting in the formation of a primary amide (benzamide). The excess ammonia ensures complete conversion to the amide.
Step 3: Analyze the reaction in part (ii). The starting material is a cyclic ester (lactone), and the reagent is NaOH followed by acid workup. NaOH hydrolyzes the lactone via nucleophilic attack on the carbonyl carbon, breaking the ring and forming a carboxylate intermediate.
Step 4: In part (ii), after hydrolysis by NaOH, the acid workup protonates the carboxylate group, resulting in the formation of a linear carboxylic acid. The hydroxyl group from the lactone remains intact, forming a hydroxy acid.
Step 5: Summarize the products: (i) The product is benzamide (C₆H₅CONH₂). (ii) The product is a hydroxy acid derived from the lactone, specifically 6-hydroxyhexanoic acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acid Derivatives
Carboxylic acid derivatives, such as esters, amides, and anhydrides, are compounds that can be derived from carboxylic acids. They retain the carboxyl functional group but have different substituents. Understanding their reactivity is crucial, as they can undergo nucleophilic acyl substitution reactions, where a nucleophile replaces the leaving group, leading to the formation of new products.
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Intro to Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group in a carboxylic acid derivative. This reaction typically involves the formation of a tetrahedral intermediate, followed by the elimination of a leaving group. In the context of the question, excess NH3 acts as the nucleophile, leading to the formation of an amide.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Acid-Base Reactions and Workup Procedures
In organic synthesis, acid-base reactions are often used to neutralize reaction mixtures or to facilitate the isolation of products. The term 'acid workup' refers to the process of adding acid to a basic reaction mixture to protonate and precipitate the desired product. In the second reaction, the use of NaOH followed by acid workup indicates that a carboxylic acid is likely formed from the reaction, which can then be isolated.
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02:49The Lewis definition of acids and bases.
Related Practice
Textbook Question
Phosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents?
c. excess propylamine
d. excess water
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Textbook Question
When a student treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.
1
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Textbook Question
What are the products of the following reactions?
c.
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Textbook Question
When butanoic acid and 18O-labeled methanol react under acidic conditions, what compounds are labeled when the reaction has reached equilibrium?
2
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Textbook Question
What are the products of the following reactions?
d.
1
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