Domanda del libro di testo
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)
998
views
Ch. 8 - Alkenes 1: Properties and Electrophilic Additions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testo
Mullins 1st EditionCh. 8 - Alkenes 1: Properties and Electrophilic AdditionsProblema 54a
Mullins 1st EditionCh. 8 - Alkenes 1: Properties and Electrophilic AdditionsProblema 54aCapitolo 7, Problema 54a
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) 
Guida verificata passo dopo passo1
Step 1: Analyze the given alkene structure. The molecule contains a phenyl group (Ph) attached to a carbon chain with a double bond located between the second and third carbons in the chain.
Step 2: For hydroboration–oxidation (1. BH3, 2. NaOH, H2O2), the reaction proceeds via anti-Markovnikov addition of water across the double bond. The boron atom initially adds to the less substituted carbon of the double bond, followed by oxidation to replace the boron with a hydroxyl group (-OH). This results in the alcohol being formed at the less substituted carbon.
Step 3: For oxymercuration–reduction (1. Hg(OAc)2, H2O, 2. NaBH4), the reaction proceeds via Markovnikov addition of water across the double bond. The mercury intermediate forms at the more substituted carbon, and during reduction, the mercury is replaced with a hydroxyl group (-OH). This results in the alcohol being formed at the more substituted carbon.
Step 4: Consider stereochemistry. Hydroboration–oxidation typically results in syn addition (both the hydrogen and hydroxyl group add to the same face of the double bond), while oxymercuration–reduction does not involve stereospecificity.
Step 5: Predict the products. For hydroboration–oxidation, the alcohol will form at the less substituted carbon of the double bond. For oxymercuration–reduction, the alcohol will form at the more substituted carbon of the double bond. Ensure the phenyl group remains unaffected in both reactions.
Risposta video verificata per un problema simile:
Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
7mConcetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Hydroboration-Oxidation
Hydroboration-oxidation is a two-step reaction that converts alkenes into alcohols. In the first step, BH₃ adds to the alkene, forming a trialkylborane intermediate. This is followed by oxidation with hydrogen peroxide (H₂O₂) and a base (NaOH), which converts the boron to an alcohol. This reaction is stereospecific and results in anti-Markovnikov addition, meaning the hydroxyl group attaches to the less substituted carbon.
Video consigliato:
06:38
General properties of hydroboration-oxidation.
Oxymercuration-Reduction
Oxymercuration-reduction is another method for converting alkenes to alcohols, involving two steps. Initially, the alkene reacts with mercuric acetate (Hg(OAc)₂) in the presence of water, leading to the formation of a mercurial intermediate. The subsequent reduction with sodium borohydride (NaBH₄) replaces the mercury with a hydrogen atom, yielding an alcohol. This reaction follows Markovnikov's rule, where the hydroxyl group attaches to the more substituted carbon.
Video consigliato:
05:General properties of oxymercuration-reduction.
Markovnikov's Rule
Markovnikov's rule is a principle in organic chemistry that predicts the outcome of electrophilic addition reactions to alkenes. It states that when HX (where X is a halogen or hydroxyl group) adds to an asymmetric alkene, the more stable carbocation will form, leading to the more substituted carbon receiving the electrophile. This rule is crucial for understanding the regioselectivity of reactions like oxymercuration-reduction, where the product distribution is influenced by the stability of the intermediates formed.
Video consigliato:
03:54The 18 and 16 Electron Rule
Pratica correlata
Domanda del libro di testo
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)
1853
views
Domanda del libro di testo
Which is more stable, a carbocation or a mercurinium ion? How do you know?
1324
views
Domanda del libro di testo
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)
1365
views
Domanda del libro di testo
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
views
Domanda del libro di testo
Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)2 , H2O 2. NaBH4 ].
(b)
1208
views