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 61
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 61Chapter 16, Problem 61
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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Identify the functional groups in the structure of aspartame. Aspartame contains ester groups, amide groups, and a carboxylic acid group. These are susceptible to hydrolysis under acidic conditions.
Understand the mechanism of hydrolysis in acidic conditions. Ester groups hydrolyze to form alcohols and carboxylic acids, while amide groups hydrolyze to form carboxylic acids and amines.
Focus on the ester bond in aspartame. The ester bond between the phenylalanine residue and the methyl group will hydrolyze to produce methanol and phenylalanine.
Examine the amide bond in aspartame. The amide bond between phenylalanine and aspartic acid will hydrolyze to produce phenylalanine and aspartic acid.
Combine the products from the hydrolysis reactions. The complete hydrolysis of aspartame in aqueous HCl will yield methanol, phenylalanine, and aspartic acid as the final products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrolysis
Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of organic compounds, hydrolysis often involves the cleavage of ester or amide bonds, leading to the formation of acids and alcohols or amines. For aspartame, hydrolysis will break it down into its constituent amino acids and methanol when treated with an acid like HCl.
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Aspartame Structure
Aspartame is a dipeptide methyl ester composed of two amino acids: aspartic acid and phenylalanine. Its structure includes an ester bond and a methyl group, which contribute to its sweetness. Understanding its structure is crucial for predicting the products of hydrolysis, as the reaction will yield the free amino acids and methanol upon complete hydrolysis.
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Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In the case of aspartame hydrolysis in an aqueous HCl solution, the acid facilitates the breakdown of the peptide bond and ester bond, leading to the formation of the products. This concept is essential for understanding how the reaction proceeds and the conditions required for complete hydrolysis.
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Related Practice
Textbook Question
What products would you expect to obtain from the following reactions?
b. methyl carbamate + methylamine
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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?
5.
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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
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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