Textbook Question
Assessment 8.74 revealed that oxymercuration could be used to make cyclic esters. Suggest a likely mechanism for this transformation.
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 117c
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 117cChapter 12, Problem 117c
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(c) Which side of the reaction would be favored by running the reaction at low temperatures?
Verified step by step guidance1
Step 1: Begin by recalling the principle of Le Chatelier's Principle, which states that a system at equilibrium will adjust to counteract changes in conditions such as temperature, pressure, or concentration.
Step 2: Understand that the acid-catalyzed dehydration reaction involves the conversion of an alcohol to an alkene and water. This reaction is reversible, meaning the equilibrium can shift toward either the reactants or products depending on the conditions.
Step 3: Consider the thermodynamics of the reaction. Dehydration reactions (formation of alkene and water) are typically endothermic, meaning they absorb heat. Conversely, the reverse reaction (hydration of the alkene) is exothermic, releasing heat.
Step 4: Apply the temperature condition given in the problem. At low temperatures, the exothermic direction (hydration of the alkene) is favored because the system will shift to release heat and counteract the lower temperature.
Step 5: Conclude that running the reaction at low temperatures would favor the side of the reaction where the alkene is hydrated back into the alcohol, shifting the equilibrium toward the reactants (alcohol and water).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Le Chatelier's Principle
Le Chatelier's Principle states that if a dynamic equilibrium is disturbed by changing the conditions, the system will adjust to counteract the change and restore a new equilibrium. In the context of acid-catalyzed dehydration, this principle helps predict how changes in temperature will affect the position of equilibrium between reactants and products.
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Reaction Equilibrium
Reaction equilibrium refers to the state in which the rates of the forward and reverse reactions are equal, resulting in constant concentrations of reactants and products. Understanding this concept is crucial for analyzing how temperature influences the favorability of either the reactants or products in a reversible reaction.
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Effect of Temperature on Reaction Direction
The effect of temperature on reaction direction is based on whether the reaction is exothermic or endothermic. Lowering the temperature favors the exothermic direction of a reversible reaction, which can help determine which side of the equilibrium will be favored under specific conditions, such as low temperatures in the dehydration reaction.
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Related Practice
Textbook Question
Suggest a mechanism for the following substitution reaction.
Textbook Question
Chapter 8 discussed the synthesis of cholesterol, which proceeds by a cationic cyclization cascade. Without looking back, suggest a mechanism by which the following reaction occurs. [The carbons have been numbered for you.]
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Textbook Question
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(b) Without looking back, how do you know this mechanism is correct?
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Textbook Question
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(a) Propose a mechanism for the formation of an alcohol from an alkene.
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Textbook Question
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(d) How might you shift the equilibrium to the right?
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