Textbook Question
Describe how the target molecule (butanone) can be synthesized in a high yield from butane.
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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 63(5)
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 63(5)Chapter 16, Problem 63(5)
a. Which of the following reactions does not give the carbonyl product shown?
b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?
5. 
Verified step by step guidance1
Step 1: Analyze the first reaction (5). The reaction involves a carbonyl compound reacting with CH3NH2 (methylamine) under heat (Δ). This is a nucleophilic addition-elimination reaction, where the amine attacks the carbonyl carbon, forming an imine (Schiff base). Consider whether this reaction would proceed under the given conditions and whether the carbonyl product would remain intact.
Step 2: Analyze the second reaction (6). The reaction involves a carbonyl compound reacting with Cl⁻ (chloride ion). Chloride is a weak nucleophile, and carbonyl compounds are generally not reactive enough to undergo nucleophilic substitution with chloride ions under neutral conditions. Consider whether this reaction would proceed and whether the carbonyl product would remain intact.
Step 3: For part (a), determine which reaction does not give the carbonyl product shown. Compare the reactivity of the carbonyl compound with the given reagents (CH3NH2 and Cl⁻) and assess whether the carbonyl group is retained or transformed in each case.
Step 4: For part (b), consider the role of an acid catalyst. Acid catalysts can protonate the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon and making it more susceptible to nucleophilic attack. Evaluate whether adding an acid catalyst would enable the reaction with Cl⁻ to proceed.
Step 5: Summarize your findings. Identify which reaction does not give the carbonyl product and explain how the addition of an acid catalyst could make the reaction occur. Ensure that your reasoning is based on the principles of nucleophilic addition and the effect of acid catalysis on carbonyl reactivity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They are key functional groups in organic chemistry, including aldehydes and ketones. Understanding the structure and reactivity of carbonyl compounds is essential for predicting the outcomes of various chemical reactions, particularly those involving nucleophiles.
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Nucleophilic Addition Reactions
Nucleophilic addition reactions involve the attack of a nucleophile on the electrophilic carbon of a carbonyl group. This reaction is fundamental in organic chemistry, as it leads to the formation of alcohols, amines, and other functional groups. Recognizing the conditions under which these reactions occur, including the presence of catalysts, is crucial for understanding the reactivity of carbonyl compounds.
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Acid Catalysis
Acid catalysis refers to the acceleration of a chemical reaction by the addition of an acid, which can enhance the electrophilicity of a carbonyl carbon. In many reactions, such as those involving carbonyl compounds, the presence of an acid can facilitate the formation of intermediates that are more reactive, thus allowing reactions that would otherwise not occur to proceed. This concept is vital for manipulating reaction pathways in organic synthesis.
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Related Practice
Textbook Question
A compound with molecular formula C5H10O2 gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the 1H NMR spectrum shown below is formed. Identify the compounds.
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Textbook Question
a. Which of the following reactions does not give the carbonyl product shown?
b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?
9.
10.
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Textbook Question
Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained if aspartame is hydrolyzed completely in an aqueous solution of HCl?
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Textbook Question
1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes transesterification reactions. Explain how it does this.
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Textbook Question
What products would you expect to obtain from the following reactions?
c. urea + water
d. β-ethylglutaric acid + acetyl chloride + Δ
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