Textbook Question
In the following three instances, which choice is greener in a chemical process? Explain. (a) A reaction that can be run at 350 K for 12 h without a catalyst or one that can be run at 300 K for 1 h with a reusable catalyst.
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Ch.18 - Chemistry of the Environment
Brown15th EditionChemistry: The Central ScienceISBN: 9780137542970
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Table of contents
- Ch.1 - Introduction: Matter, Energy, and Measurement146
- Ch.2 - Atoms, Molecules, and Ions200
- Ch.3 - Chemical Reactions and Reaction Stoichiometry176
- Ch.4 - Reactions in Aqueous Solution155
- Ch.5 - Thermochemistry126
- Ch.6 - Electronic Structure of Atoms131
- Ch.7 - Periodic Properties of the Elements126
- Ch.8 - Basic Concepts of Chemical Bonding123
- Ch.9 - Molecular Geometry and Bonding Theories143
- Ch.10 - Gases147
- Ch.11 - Liquids and Intermolecular Forces91
- Ch.12 - Solids and Modern Materials122
- Ch.13 - Properties of Solutions126
- Ch.14 - Chemical Kinetics174
- Ch.15 - Chemical Equilibrium101
- Ch.16 - Acid-Base Equilibria139
- Ch.17 - Additional Aspects of Aqueous Equilibria146
- Ch.18 - Chemistry of the Environment72
- Ch.19 - Chemical Thermodynamics129
- Ch.20 - Electrochemistry142
- Ch.21 - Nuclear Chemistry101
- Ch.22 - Chemistry of the Nonmetals68
- Ch.23 - Transition Metals and Coordination Chemistry66
- Ch.24 - The Chemistry of Life: Organic and Biological Chemistry10
Brown15th EditionChemistry: The Central ScienceISBN: 9780137542970Not the one you use?Change textbook
Chapter 18, Problem 53a
A reaction for converting ketones to lactones, called the Baeyer–Villiger reaction,
is used in the manufacture of plastics and pharmaceu- ticals. 3-Chloroperbenzoic acid is shock-sensitive, how- ever, and prone to explode. Also, 3-chlorobenzoic acid is a waste product. An alternative process being developed uses hydrogen peroxide and a catalyst consisting of tin deposited within a solid support. The catalyst is readily recovered from the reaction mixture. (a) What would you expect to be the other product of oxidation of the ketone to lactone by hydrogen peroxide?
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Identify the reactants and products in the given Baeyer–Villiger reaction: ketone and 3-chloroperbenzoic acid react to form lactone and 3-chlorobenzoic acid.
Understand that in the alternative process, hydrogen peroxide (H2O2) is used as the oxidizing agent instead of 3-chloroperbenzoic acid.
Recognize that the Baeyer–Villiger reaction involves the insertion of an oxygen atom from the oxidizing agent into the carbon-carbon bond adjacent to the carbonyl group of the ketone, forming a lactone.
Determine that the other product of the reaction must come from the decomposition of hydrogen peroxide.
Conclude that the other product of the oxidation of the ketone to lactone by hydrogen peroxide is water (H2O), as hydrogen peroxide decomposes into water and oxygen.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Baeyer–Villiger Reaction
The Baeyer–Villiger reaction is an organic reaction that involves the oxidation of ketones to form esters or lactones using peracids. This reaction is significant in synthetic organic chemistry, particularly in the production of cyclic esters (lactones) from cyclic ketones. The mechanism involves the formation of a peracid intermediate, which rearranges to yield the lactone and a carboxylic acid as byproducts.
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Oxidation and Reduction
Oxidation refers to the process of losing electrons or increasing oxidation state, while reduction involves gaining electrons or decreasing oxidation state. In the context of the Baeyer–Villiger reaction, the ketone undergoes oxidation to form a lactone, which is a cyclic ester. Understanding these concepts is crucial for predicting the products of chemical reactions and the changes in oxidation states of the reactants.
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Catalysis
Catalysis is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst, which is not consumed in the reaction. In the alternative process mentioned, hydrogen peroxide is used as an oxidizing agent, and a tin-based catalyst facilitates the reaction. The use of catalysts is essential in industrial chemistry to enhance efficiency and selectivity while minimizing waste and energy consumption.
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