Textbook Question
Thiols are prone to dimerize through the formation of a disulfide bond in a reaction that stylists use to induce permanent curls in hair. What type of reagent would you use to effect this transformation?
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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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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. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 111
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 111Chapter 12, Problem 111
We explain in Chapter 24 that bisphenols can be oxidized to quinones.
(a) Calculate the oxidation numbers of C1 and C₂ in going from reactant to product.
(b) Provide a mechanism for this transformation. [The reaction begins like the alcohol oxidations of Section 13.9.]
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Identify the structure of the reactant and product. The reactant is a bisphenol with hydroxyl groups on C1 and C2, and the product is a quinone with carbonyl groups on C1 and C2.
Calculate the oxidation number of C1 and C2 in the reactant. In the bisphenol, each carbon (C1 and C2) is bonded to an -OH group and two other carbons. Assign oxidation numbers based on these bonds.
Calculate the oxidation number of C1 and C2 in the product. In the quinone, each carbon (C1 and C2) is bonded to an oxygen (double bond) and two other carbons. Assign oxidation numbers based on these bonds.
Compare the oxidation numbers of C1 and C2 in the reactant and product to determine the change in oxidation state, indicating oxidation.
Outline the mechanism for the transformation. The reaction begins with the formation of a chromate ester intermediate, followed by elimination to form the carbonyl groups, similar to alcohol oxidation mechanisms.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Numbers
Oxidation numbers are a way to keep track of electron transfer in chemical reactions. They indicate the degree of oxidation of an atom in a compound, helping to identify how many electrons are lost or gained. In the context of the transformation from bisphenols to quinones, calculating the oxidation numbers of specific carbon atoms (C1 and C2) allows us to understand the changes in electron density and the overall oxidation state during the reaction.
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Mechanism of Oxidation
The mechanism of oxidation describes the step-by-step process by which a reactant is converted into a product through the breaking and forming of bonds. In the case of bisphenols oxidizing to quinones, the mechanism typically involves the removal of hydrogen atoms and the formation of double bonds, which can be illustrated using curved arrows to show electron movement. Understanding this mechanism is crucial for predicting the behavior of similar organic reactions.
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Alcohol Oxidation
Alcohol oxidation refers to the chemical process where alcohols are converted into carbonyl compounds, such as aldehydes or ketones, often involving the loss of hydrogen. This process is fundamental in organic chemistry and serves as a basis for understanding more complex transformations, such as the oxidation of bisphenols to quinones. Familiarity with the principles of alcohol oxidation helps in grasping the underlying reactions and mechanisms involved in the transformation discussed in the question.
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Related Practice
Textbook Question
Triphenylphosphine and iodine can be used to convert alcohols to iodoalkanes. Suggest a mechanism for this reaction. [Triphenylphosphine first acts as a nucleophile in this reaction.]
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Textbook Question
Cleavage of the following ether produces the alcohol and haloalkane only, regardless of how much HBr is used. Thinking about the mechanism of the reaction, explain why bromobenzene is not also a product of this reaction.
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Textbook Question
A chemist attempted the reaction below, one we introduce in Chapter 17, expecting the reaction between a strong nucleophile and a ketone in water to give an alkoxide product.
(a) Why did the reaction fail?
(b) How could the reaction conditions be changed to give a successful reaction?
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Textbook Question
In Chapter 12, we learned that crown ethers were used to increase the rate of SN2 reactions (Assessment 12.80). Suggest a synthesis of 15-crown-5 using the reactions learned here in Chapter 13.
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Textbook Question
Another method for converting alcohols to chloroalkanes makes use of chlorotrimethylsilane (TMSCl) and DMSO. Suggest a mechanism for this reaction to form (a) a 1° chloroalkane and (b) a 3° chloroalkane. [The reaction begins by the reaction of DMSO and TMSCl and is analogous to the Swern oxidation.]
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