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.
(a)
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 54b(ii)
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 54b(ii)Chapter 7, Problem 54b(ii)
Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)2 , H2O 2. NaBH4 ].
(b) 
Verified step by step guidance1
Step 1: Identify the alkene structure in the given image. The structure is a cyclodecene, a cyclic compound with a double bond in a 10-membered ring.
Step 2: Recall the mechanism of oxymercuration-reduction. In the first step, Hg(OAc)2 and H2O are used to add a hydroxyl group (-OH) to the more substituted carbon of the double bond, following Markovnikov's rule. This avoids carbocation rearrangements.
Step 3: Understand that the addition of the hydroxyl group occurs without stereoselectivity in the first step. The intermediate formed is an organomercury compound.
Step 4: In the second step, NaBH4 is used to reduce the organomercury intermediate, replacing the mercury group with a hydrogen atom. This completes the formation of the alcohol product.
Step 5: Predict the final product. The double bond in cyclodecene will be converted into an alcohol group (-OH) attached to the more substituted carbon of the original double bond, resulting in a Markovnikov alcohol 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. The first step involves the addition of mercuric acetate (Hg(OAc)2) and water to the alkene, forming a mercurial intermediate. In the second step, sodium borohydride (NaBH4) is used to reduce the mercurial compound to an alcohol, resulting in Markovnikov addition of water across the double bond.
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General properties of oxymercuration-reduction.
Markovnikov's Rule
Markovnikov's Rule states that when HX (where X is a halogen or OH) is added to an asymmetric alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of electrophilic addition reactions, ensuring that the more stable carbocation intermediate is formed during the reaction.
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Alkene Reactivity
Alkenes are reactive due to the presence of a carbon-carbon double bond, which is a site of high electron density. This reactivity allows alkenes to undergo various addition reactions, including electrophilic additions like oxymercuration. The structure and substitution pattern of the alkene influence the reaction pathway and the stability of intermediates, which are crucial for predicting the products formed.
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Related Practice
Textbook Question
Suggest an alkene to undergo hydroboration–oxidation (1. BH3 2. NaOH, H2O2) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.
(d)
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Textbook Question
Suggest an alkene to undergo hydroboration–oxidation (1. BH3 2. NaOH, H2O2) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.
(c)
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Textbook Question
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(e)
1
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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)
1
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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)
2
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