Textbook Question
Benzyl ethers make excellent protecting groups according to the general scheme shown here.
(a) How would you protect the 1° alcohol as a benzyl ether in the first step?
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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 113
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 113Chapter 12, Problem 113
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?
Verified step by step guidance1
Identify the starting material and the product: The starting material is a thiol (R-SH) and the product is a disulfide (R-S-S-R).
Recognize the type of reaction: This is an oxidation reaction where two thiol groups are converted into a disulfide bond.
Determine the type of reagent needed: An oxidizing agent is required to facilitate the formation of the disulfide bond from the thiol groups.
Consider common oxidizing agents for thiol to disulfide conversion: Common reagents include iodine (I2), hydrogen peroxide (H2O2), or atmospheric oxygen (O2) under certain conditions.
Select an appropriate reagent: Choose an oxidizing agent that is suitable for the reaction conditions and desired reaction rate, such as iodine in an aqueous or organic solvent.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Thiol Chemistry
Thiols, or mercaptans, are organic compounds containing a sulfhydryl group (-SH). They are known for their strong odors and are important in various biological processes. In the context of hair styling, thiols can undergo oxidation to form disulfide bonds, which are crucial for the structural integrity of proteins, including keratin in hair.
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The mechanism of Sulfide Synthesis.
Disulfide Bond Formation
Disulfide bonds are covalent linkages formed between the sulfur atoms of two thiol groups. This reaction is typically facilitated by an oxidizing agent, which removes hydrogen atoms from the thiols, allowing the sulfur atoms to bond. Disulfide bonds play a significant role in stabilizing the three-dimensional structure of proteins, influencing their functionality and properties.
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Oxidizing Agents
Oxidizing agents are substances that can accept electrons from another species, thereby facilitating oxidation reactions. In the case of thiols, common oxidizing agents include hydrogen peroxide and iodine, which can promote the formation of disulfide bonds. Understanding the choice of oxidizing agent is essential for controlling the extent and specificity of the reaction in applications like hair curling.
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Related Practice
Textbook Question
Suggest a mechanism for the following substitution 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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Textbook Question
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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