Domanda del libro di testo
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (vi) NaOH, H2O . If there is no reaction, write 'no reaction.'
(a)
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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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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
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 88a(ii)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 88a(ii)Capitolo 12, Problema 88a(ii)
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)2 2. NaBH4.If there is no reaction, write 'no reaction.'
(a) 
Guida verificata passo dopo passo1
Step 1: Recognize the reaction type. The reagents provided, Hg(OAc)₂ followed by NaBH₄, indicate an oxymercuration-demercuration reaction. This reaction is used to hydrate alkenes (add water across a double bond) without carbocation rearrangement.
Step 2: Identify the functional group in the starting molecule. Check if the molecule contains an alkene (C=C double bond), as this reaction specifically targets alkenes.
Step 3: Understand the mechanism. In the first step, Hg(OAc)₂ reacts with the alkene to form a mercurinium ion intermediate. Water then attacks the more substituted carbon of the intermediate, leading to the addition of an -OH group. In the second step, NaBH₄ reduces the mercury group, replacing it with a hydrogen atom.
Step 4: Predict the product. The final product will be an alcohol, with the -OH group added to the more substituted carbon of the original double bond (Markovnikov addition). If the starting molecule does not contain an alkene, there will be no reaction.
Step 5: Verify the conditions. Ensure that the reaction conditions are suitable for the starting molecule. If the molecule lacks a double bond or has functional groups incompatible with the reaction, write 'no reaction.'
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Concetti chiave
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Mercuration-Demercuration
The mercuration-demercuration reaction is a two-step process used to convert alkenes into alcohols. In the first step, mercuric acetate (Hg(OAc)₂) adds to the double bond of the alkene, forming a mercurinium ion. The second step involves the reduction of this intermediate by sodium borohydride (NaBH₄), which replaces the mercury with a hydrogen atom, yielding an alcohol.
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General properties of oxymercuration-reduction.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of mercuration, the reaction typically follows Markovnikov's rule, where the more substituted carbon atom of the alkene becomes bonded to the mercury, leading to the formation of the more stable carbocation intermediate.
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05:09Heck Reaction
Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In the context of the mercuration-demercuration process, sodium borohydride acts as a reducing agent, facilitating the conversion of the mercurinium ion to an alcohol by donating electrons and protons, effectively replacing the mercury with a hydrogen atom.
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07:12Reductive Amination
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