Textbook Question
a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
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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 79
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 79Chapter 16, Problem 79
Identify the major and minor products of the following reaction:
Verified step by step guidance1
Step 1: Analyze the reactants. The molecule contains two nucleophilic functional groups: a primary amine (-NH2) and a secondary amine (-NH). Both can react with the electrophilic acetyl chloride (CH3COCl). The hydroxyl group (-OH) is less nucleophilic and unlikely to react under these conditions.
Step 2: Consider the reaction conditions. Since only 1 equivalent of acetyl chloride is provided, only one nucleophilic site will react. The primary amine (-NH2) is more nucleophilic than the secondary amine (-NH) due to less steric hindrance and higher electron density.
Step 3: Predict the major product. The primary amine will likely react with acetyl chloride to form an amide bond. The reaction mechanism involves nucleophilic attack by the amine on the carbonyl carbon of acetyl chloride, followed by the elimination of HCl.
Step 4: Predict the minor product. If the secondary amine reacts instead, it will form a different amide product. However, this is less likely due to steric hindrance and the lower nucleophilicity of the secondary amine compared to the primary amine.
Step 5: Summarize the outcome. The major product will be the amide formed from the reaction of the primary amine with acetyl chloride. The minor product, if formed, would result from the reaction of the secondary amine with acetyl chloride.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks a carbonyl carbon, leading to the replacement of a leaving group. This reaction is characteristic of carboxylic acid derivatives, such as esters, amides, and acyl chlorides. Understanding this mechanism is crucial for predicting the major and minor products formed during the reaction.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Carboxylic Acid Derivatives
Carboxylic acid derivatives include compounds like acyl chlorides, esters, and amides, which can undergo nucleophilic acyl substitution. Each derivative has different reactivity due to the nature of the leaving group and the electrophilicity of the carbonyl carbon. Recognizing the type of derivative involved in the reaction helps in determining the expected products.
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Product Distribution
In reactions involving nucleophilic acyl substitution, the distribution of products can be classified as major and minor based on factors such as sterics, electronics, and the stability of the resulting compounds. Major products are typically more stable or formed in greater quantities, while minor products may arise from less favorable pathways. Analyzing these factors is essential for predicting the outcome of the reaction.
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Related Practice
Textbook Question
Cardura, a drug used to treat hypertension, is synthesized as shown here.
b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?
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Textbook Question
a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
c. If an ester is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, where will the label reside in the product?
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Textbook Question
a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethanol. Why? (HINT: Build models.)
b. Would he have encountered the same problem if he had tried to synthesize the methyl ester of 4-methylbenzoic acid in the same way?
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Textbook Question
When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.
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Textbook Question
Cardura, a drug used to treat hypertension, is synthesized as shown here.
a. Identify the intermediate (A) and show the mechanism for its formation.
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