Textbook Question
b. Explain why the rate of aminolysis of an ester cannot be increased by H+.
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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 31a
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 31aChapter 16, Problem 31a
Show how each of the following esters could be prepared using a carboxylic acid as one of the starting materials:
a. methyl butyrate (odor of apples)
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Identify the structure of methyl butyrate. Methyl butyrate is an ester with the formula CH₃CH₂CH₂COOCH₃. It consists of a butanoic acid-derived portion (CH₃CH₂CH₂CO-) and a methyl group (-OCH₃).
Recall the general method for ester synthesis: Esters are typically prepared via Fischer esterification, which involves reacting a carboxylic acid with an alcohol in the presence of an acid catalyst (e.g., H₂SO₄).
Determine the carboxylic acid and alcohol needed to form methyl butyrate. The carboxylic acid must be butanoic acid (CH₃CH₂CH₂COOH), and the alcohol must be methanol (CH₃OH).
Write the reaction equation for the synthesis: CH₃CH₂CH₂COOH + CH₃OH → CH₃CH₂CH₂COOCH₃ + H₂O. This reaction is catalyzed by an acid, such as H₂SO₄, to promote the formation of the ester bond.
Describe the reaction conditions: Combine butanoic acid and methanol in a reaction flask, add a few drops of concentrated sulfuric acid as the catalyst, and heat the mixture under reflux. After the reaction is complete, the ester can be purified by distillation or extraction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Esterification
Esterification is a chemical reaction that forms an ester from a carboxylic acid and an alcohol. This process typically involves the condensation of the two reactants, resulting in the elimination of water. The reaction can be catalyzed by an acid, which helps to increase the reaction rate. Understanding this process is crucial for synthesizing esters like methyl butyrate.
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Reactions of Amino Acids: Esterification Concept 1
Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are key starting materials in ester synthesis, as they provide the acid component needed for esterification. The specific carboxylic acid used will influence the structure and properties of the resulting ester, making it essential to select the appropriate acid for the desired ester.
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04:20Carboxylic Acids Nomenclature
Alcohols
Alcohols are organic compounds containing one or more hydroxyl groups (-OH) attached to a carbon atom. In the context of ester synthesis, the choice of alcohol is critical, as it determines the alkyl portion of the ester. For methyl butyrate, methanol is the alcohol used, and understanding its role in the esterification process is vital for successful synthesis.
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01:01How to name alcohols
Related Practice
Textbook Question
Propose a mechanism for the following reaction. (Hint: Number the carbons to help you see where they end up in the product.)
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Textbook Question
Which of the following reactions lead to the formation of an amide?
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Textbook Question
D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C—O bond, rather than the alkyl C—O bond, by studying the hydrolysis of the following ester under basic conditions:
a. What products contained the 18O label?
b. What product would have contained the 18O label if the alkyl C—O bond had broken?
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Textbook Question
b. Explain why the rate of aminolysis of an ester cannot be increased by HO−, or RO−.
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Textbook Question
What acyl chloride and amine are required to synthesize the following amides?
a. N-ethylbutanamide
b. N,N-dimethylbenzamide
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