Textbook Question
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
c.
d.
1
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 51
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 51Chapter 11, Problem 51
The following three nitrogen mustards were studied for possible clinical use. One is now used clinically, one was found to be too unreactive, and one was found to be too insoluble in water to be injected intravenously. Which is which? (Hint: Draw resonance contributors.)
Verified step by step guidance1
Step 1: Analyze the chemical structures of the three nitrogen mustards provided in the image. The first compound has a phenyl group attached to the nitrogen atom, the second compound has a methyl group attached to the nitrogen atom, and the third compound has a phenyl group with a carbonyl group attached to the nitrogen atom.
Step 2: Consider the reactivity of each compound. The nitrogen atom in the first compound is conjugated with the aromatic ring, allowing resonance stabilization. This delocalization reduces the nucleophilicity of the nitrogen and makes the compound less reactive.
Step 3: Evaluate the solubility of each compound. The third compound has a carbonyl group attached to the aromatic ring, which increases polarity and hydrogen bonding potential. This makes the compound more water-soluble compared to the other two.
Step 4: Compare the second compound to the others. The nitrogen atom in the second compound is not conjugated with an aromatic ring, and it lacks additional polar functional groups. This makes it more reactive and less water-soluble than the other two compounds.
Step 5: Based on the analysis, assign the clinical use, reactivity, and solubility properties: The second compound is likely the one used clinically due to its reactivity. The first compound is too unreactive due to resonance stabilization. The third compound is too water-soluble due to the carbonyl group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nitrogen Mustards
Nitrogen mustards are a class of alkylating agents derived from mustard gas, characterized by a nitrogen atom in their structure. They are used in chemotherapy due to their ability to form covalent bonds with DNA, leading to cell death. Understanding their chemical properties, such as reactivity and solubility, is crucial for evaluating their clinical applications.
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Nitrogenous Bases Concept 2
Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In nitrogen mustards, resonance can affect the stability and reactivity of the compound. Analyzing resonance contributors helps predict how these compounds will behave in biological systems, influencing their clinical effectiveness.
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03:04Drawing Resonance Structures
Solubility and Reactivity
Solubility and reactivity are key factors in determining the clinical use of chemical compounds. A compound must be soluble enough to be administered intravenously, while also being reactive enough to interact with biological targets. Understanding the balance between these properties is essential for assessing which nitrogen mustard is suitable for clinical use.
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01:17Reactivity of Molecules
Related Practice
Textbook Question
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
b.
Textbook Question
What is the product of each of the following reactions?
c.
d.
1
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Textbook Question
Why is melphalan a good cancer drug?
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Textbook Question
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
a.
1
views
Textbook Question
What is the product of each of the following reactions?
a.
1
views