Domanda del libro di testo
Draw a mechanism for the following oxidation reactions.
(c)
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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 103
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 103Capitolo 12, Problema 103
In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Williamson ether synthesis to make the ether shown. Identify the combination and explain why it is the only combination that works.
Guida verificata passo dopo passo1
Identify the ether product: The ether shown is isopropyl phenyl ether, which consists of an isopropyl group and a phenyl group connected by an oxygen atom.
Understand the Williamson ether synthesis: This reaction involves the reaction of an alkoxide ion with a haloalkane to form an ether. The alkoxide ion acts as a nucleophile, attacking the electrophilic carbon in the haloalkane.
Determine the possible alkoxide: The alkoxide must correspond to the part of the ether that is less hindered. In this case, the phenoxide ion (C6H5O-) is less hindered compared to the isopropyl group.
Select the appropriate haloalkane: The haloalkane should be the more hindered part of the ether, which is the isopropyl group. Therefore, the haloalkane should be isopropyl bromide (or chloride).
Explain why this combination works: The phenoxide ion is a strong nucleophile and can effectively attack the less hindered primary carbon in isopropyl bromide, leading to the formation of isopropyl phenyl ether. Other combinations would lead to steric hindrance or less favorable reactions.
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Williamson Ether Synthesis
The Williamson ether synthesis is a method for creating ethers by reacting an alkoxide ion with a haloalkane. This reaction typically involves a nucleophilic substitution mechanism, where the alkoxide acts as a nucleophile and attacks the electrophilic carbon in the haloalkane, displacing the halide ion. The choice of haloalkane and alkoxide is crucial, as steric hindrance and the nature of the leaving group can significantly affect the reaction's success.
Video consigliato:
03:50
The Mechanism of Williamson Ether Synthesis.
Nucleophilicity and Electrophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair to form a chemical bond, while electrophilicity is the ability of a species to accept an electron pair. In the context of the Williamson ether synthesis, the alkoxide is a strong nucleophile due to its negative charge, and the haloalkane must be a suitable electrophile, typically a primary or methyl halide, to facilitate the reaction without steric hindrance that would impede nucleophilic attack.
Video consigliato:
03:Nucleophile or Electrophile
Steric Hindrance
Steric hindrance is the prevention of chemical reactions due to the spatial arrangement of atoms within a molecule. In the Williamson ether synthesis, using a bulky haloalkane can hinder the approach of the nucleophile, making the reaction less favorable or impossible. Therefore, the selection of a primary haloalkane is often necessary to ensure that steric factors do not obstruct the nucleophilic attack by the alkoxide.
Video consigliato:
02:53Understanding steric effects.
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Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
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Draw a mechanism for the following oxidation reactions.
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