Textbook Question
What reagents would you use to convert methyl propanoate to the following compounds?
c. N-ethylpropanamide
d. propanoic acid
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 59a
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 59aChapter 16, Problem 59a
What products would you expect to obtain from the following reactions?
a. malonic acid + 2 acetyl chloride
Verified step by step guidance1
Step 1: Recognize the functional groups in the reactants. Malonic acid contains two carboxylic acid groups (-COOH), and acetyl chloride is an acid chloride (-COCl). Acid chlorides are highly reactive and can undergo acylation reactions with nucleophiles like the hydroxyl groups in malonic acid.
Step 2: Understand the reaction mechanism. The hydroxyl group (-OH) of malonic acid will act as a nucleophile and attack the carbonyl carbon of acetyl chloride. This results in the formation of an ester bond and the release of HCl as a byproduct.
Step 3: Consider the stoichiometry of the reaction. Since there are two hydroxyl groups in malonic acid and two molecules of acetyl chloride, each hydroxyl group can react with one acetyl chloride molecule, leading to the formation of a diester.
Step 4: Write the structure of the product. The product will be a diester where both carboxylic acid groups of malonic acid are converted into ester groups by reacting with acetyl chloride. The general structure will be CH2(COOR)2, where R is the acetyl group (CH3CO).
Step 5: Account for byproducts. Each reaction between a hydroxyl group and acetyl chloride releases HCl as a byproduct. Since two acetyl chloride molecules are used, two molecules of HCl will be produced in this reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Malonic Acid
Malonic acid is a dicarboxylic acid with the formula C3H4O4. It contains two carboxyl groups (-COOH) and is commonly used in organic synthesis. Its structure allows it to undergo various reactions, including esterification and acylation, making it a versatile building block in the synthesis of more complex molecules.
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General Reactions
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are derivatives of carboxylic acids where the hydroxyl group is replaced by a chlorine atom. They are highly reactive and are often used in acylation reactions to introduce acyl groups into organic compounds. In the presence of nucleophiles, acyl chlorides readily react to form esters, amides, or other acyl derivatives.
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01:57Recognizing acyl chlorides and anhydrides.
Reactions of Malonic Acid with Acyl Chlorides
When malonic acid reacts with acyl chlorides, it typically undergoes a reaction known as acylation, leading to the formation of malonic acid derivatives. In this case, two acetyl chlorides would introduce two acetyl groups into the malonic acid structure, resulting in the formation of a diacetyl derivative. This reaction is significant in synthetic organic chemistry for constructing complex molecules.
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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 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
What reagents would you use to convert methyl propanoate to the following compounds?
a. isopropyl propanoate
b. sodium propanoate
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Textbook Question
Using an alcohol for one method and an alkyl halide for the other, show two ways to make each of the following esters:
d. methyl phenylethanoate (odor of honey)
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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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