Textbook Question
Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
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. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 53a
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 53aChapter 7, Problem 53a
Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.
(a) 
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Identify the target ether structure and determine the position of the oxygen atom in the final product. This will help in identifying the alkene and the alcohol needed for the reaction.
Select an alkene that, upon oxymercuration, will lead to the formation of a carbocation at the position where the ether linkage is desired. This is typically the more substituted carbon of the double bond.
Choose the appropriate alcohol that will act as the nucleophile in the reaction. The alcohol will attack the carbocation formed during the oxymercuration step, leading to the formation of the ether linkage.
Set up the reaction conditions for oxymercuration. This typically involves using mercuric acetate (Hg(OAc)2) in a solvent like THF (tetrahydrofuran) with the chosen alcohol. This step forms the mercurinium ion intermediate.
Perform the reduction step using sodium borohydride (NaBH4) in a basic aqueous solution. This step will remove the mercury group and complete the formation of the ether product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxymercuration–Reduction
Oxymercuration–reduction is a two-step reaction used to convert alkenes into alcohols or ethers without carbocation rearrangement. The first step involves the addition of mercuric acetate to the alkene, forming a mercurinium ion intermediate. In the second step, sodium borohydride (NaBH4) reduces the intermediate, replacing the mercury with a hydrogen atom, resulting in the formation of an alcohol or ether.
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05:
General properties of oxymercuration-reduction.
Alkene Selection
Choosing the correct alkene is crucial for synthesizing the desired ether. The alkene's structure determines the position where the ether linkage will form. Typically, the alkene should have a double bond at the location where the ether's oxygen will be introduced, ensuring the correct regioselectivity and stereochemistry in the final product.
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2:09Alkene Metathesis Concept 1
Reaction Conditions for Ether Synthesis
To synthesize ethers using oxymercuration–reduction, the reaction conditions must be carefully controlled. The process involves using an alcohol as a nucleophile instead of water in the oxymercuration step. This modification allows the formation of an ether linkage instead of an alcohol, with the alcohol's oxygen attacking the mercurinium ion, leading to the desired ether product after reduction.
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03:50The Mechanism of Williamson Ether Synthesis.
Related Practice
Textbook Question
Which is more stable, a carbocation or a mercurinium ion? How do you know?
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Textbook Question
Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.
(b)
1167
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Textbook Question
Predict the products you would get when the following alkenes undergo (i) hydroboration–oxidation (1. BH3 2. NaOH, H2O2 or (ii) oxymercuration–reduction [1. Hg(OAc)2, H2O 2. NaBH4].
(a)
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Textbook Question
Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)2 , H2O 2. NaBH4 ].
(b)
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Textbook Question
Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.
1278
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