Textbook Question
What are the products of the following reactions?
c.
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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 64
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 64Chapter 16, Problem 64
Describe how the target molecule (butanone) can be synthesized in a high yield from butane.
Verified step by step guidance1
Step 1: Begin by understanding the transformation required. The target molecule, butanone (CH3COCH2CH3), is a ketone, while the starting material, butane (C4H10), is an alkane. This means the process will involve oxidation to introduce a carbonyl group.
Step 2: Perform a controlled oxidation of butane. First, convert butane into butanol (an alcohol) by reacting it with oxygen in the presence of a catalyst, such as cobalt or manganese-based catalysts. This step is crucial to introduce a functional group that can be further oxidized.
Step 3: Oxidize the butanol to butanal (an aldehyde). This can be achieved using a mild oxidizing agent such as PCC (Pyridinium chlorochromate) or by carefully controlling the reaction conditions with stronger oxidizing agents like KMnO4 or CrO3.
Step 4: Further oxidize butanal to butanone. This step involves converting the aldehyde group (-CHO) into a ketone group (-CO-). A strong oxidizing agent such as potassium dichromate (K2Cr2O7) in acidic conditions can be used for this transformation.
Step 5: Ensure high yield by carefully controlling reaction conditions at each step. For example, avoid over-oxidation of butanone to carboxylic acids by monitoring the reaction time and using appropriate catalysts. Purify the final product using distillation or other separation techniques.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrocarbon Functional Groups
Understanding the functional groups in hydrocarbons is essential for organic synthesis. Butane is an alkane, characterized by single bonds between carbon atoms, while butanone is a ketone, which contains a carbonyl group (C=O) flanked by two carbon atoms. Recognizing these functional groups helps in determining the necessary reactions to convert butane into butanone.
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Identifying Functional Groups
Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state, which is crucial for converting alkanes to ketones. In the case of butane to butanone, a common method is the oxidation of butane using reagents like potassium permanganate or chromic acid, which facilitates the transformation of the alkane into the corresponding ketone while maximizing yield.
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Reaction Conditions and Yield
The conditions under which a reaction occurs significantly affect the yield of the desired product. Factors such as temperature, pressure, and the presence of catalysts can influence the efficiency of the oxidation process. Optimizing these conditions is vital for achieving a high yield of butanone from butane, ensuring that side reactions are minimized and the desired product is favored.
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04:37Draw all of the monochlorination products and calculate percentage yields.
Related Practice
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?
5.
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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
What are the products of the following reactions?
a.
b.
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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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