Textbook Question
What are the products of the base hydrolysis of an ester?
Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353
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Table of contents
- Ch.1 Chemistry in Our Lives11
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy54
- Ch.4 Atoms and Elements51
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions41
- Ch.8 Gases29
- Ch.9 Solutions51
- Ch.10 Acids and Bases and Equilibrium65
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons78
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones83
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides90
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis83
- Ch.18 Metabolic Pathways and ATP Production67
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 14, Problem 28a
Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:
a. 
Verified step by step guidance1
Identify the functional group in the given compound. Hydrolysis typically involves breaking a bond in a molecule using water, often targeting esters, amides, or other hydrolyzable groups.
Determine whether the reaction is acid-catalyzed or base-catalyzed. Acid-catalyzed hydrolysis typically involves protonation of the functional group to make it more reactive, while base-catalyzed hydrolysis involves nucleophilic attack by hydroxide ions.
For acid-catalyzed hydrolysis: Protonate the functional group (e.g., ester or amide) to make it more electrophilic. Then, water acts as a nucleophile, attacking the carbonyl carbon, leading to the formation of an intermediate. This intermediate eventually breaks down to form the products.
For base-catalyzed hydrolysis: Hydroxide ions directly attack the carbonyl carbon of the functional group, leading to the cleavage of the bond and formation of the products. For esters, this typically results in a carboxylate ion and an alcohol.
Draw the condensed structural or line-angle formulas for the products based on the type of hydrolysis (acid or base) and the specific functional group in the starting compound. Ensure the products are correctly represented with their respective functional groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Catalysis
Acid-base catalysis involves the acceleration of a chemical reaction by the presence of an acid or a base. In hydrolysis reactions, acids can donate protons to facilitate the breaking of bonds, while bases can accept protons to stabilize intermediates. Understanding this concept is crucial for predicting the products formed during hydrolysis.
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Arrhenius Acids & Bases Concept 1
Hydrolysis
Hydrolysis is a chemical reaction in which water is used to break down a compound. In organic chemistry, this often involves the cleavage of bonds in larger molecules, resulting in the formation of smaller products. Recognizing the type of hydrolysis (acidic or basic) is essential for determining the resulting structures.
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Condensed Structural and Line-Angle Formulas
Condensed structural formulas provide a shorthand way to represent the structure of a molecule, showing how atoms are connected without depicting all bonds explicitly. Line-angle formulas, on the other hand, use lines to represent bonds and vertices to represent carbon atoms, simplifying the visualization of complex organic structures. Mastery of these representations is vital for accurately illustrating the products of hydrolysis.
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Related Practice
Textbook Question
Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:
a.
Textbook Question
Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:
b.
Textbook Question
Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:
d.
Textbook Question
Write the common name for each of the following:
b.
Textbook Question
Write the common name for each of the following:
c.
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