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 117d
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 117dChapter 12, Problem 117d
The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.
(d) How might you shift the equilibrium to the right?
Verified step by step guidance1
Step 1: Recognize that the reaction shown is an equilibrium between an alkene and an alcohol, catalyzed by sulfuric acid (H₂SO₄). The forward reaction involves hydration of the alkene to form the alcohol, while the reverse reaction involves dehydration of the alcohol to form the alkene.
Step 2: Apply Le Chatelier's Principle, which states that a system at equilibrium will shift to counteract changes in concentration, pressure, or temperature. To shift the equilibrium to the right (toward the alcohol), you need to favor the hydration reaction.
Step 3: Increase the concentration of water (H₂O) in the reaction mixture. Adding excess water will drive the equilibrium toward the alcohol product, as the system will attempt to reduce the concentration of water by forming more alcohol.
Step 4: Remove the alcohol product as it forms. By continuously removing the alcohol from the reaction mixture, the equilibrium will shift to the right to produce more alcohol to replace what was removed.
Step 5: Lower the temperature if the hydration reaction is exothermic. If the forward reaction releases heat, lowering the temperature will favor the formation of the alcohol product according to Le Chatelier's Principle.
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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 position of equilibrium shifts to counteract the change. In the context of acid-catalyzed dehydration, altering concentration, temperature, or pressure can influence the direction of the reaction, favoring either the formation of products or reactants.
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04:12
The Electron Configuration
Equilibrium Constant (K)
The equilibrium constant (K) quantifies the ratio of the concentrations of products to reactants at equilibrium for a given reaction at a specific temperature. A larger K value indicates a greater concentration of products at equilibrium, suggesting that the reaction favors product formation. Understanding K helps predict how changes in conditions will affect the equilibrium position.
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02:19The relationship between equilibrium constant and pKa.
Acid-Base Catalysis
Acid-base catalysis involves the acceleration of a reaction by an acid or base, which donates or accepts protons (H+ ions). In acid-catalyzed dehydration, the presence of an acid facilitates the removal of water from alcohols, promoting the formation of alkenes. Recognizing the role of the catalyst is crucial for understanding how to manipulate the reaction conditions to shift the equilibrium.
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Related Practice
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.
(c) Which side of the reaction would be favored by running the reaction at low temperatures?
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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
Suggest reagents to carry out the following transformation.
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