Textbook Question
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
c.
d.
1448
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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 52
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 52Chapter 11, Problem 52
Why is melphalan a good cancer drug?
Verified step by step guidance1
Melphalan is a type of alkylating agent, which means it works by adding alkyl groups to DNA. This disrupts the DNA structure and function, preventing cancer cells from replicating effectively.
The drug specifically targets rapidly dividing cells, such as cancer cells, because these cells are more vulnerable to DNA damage during replication. This selectivity makes melphalan effective in treating cancer.
Melphalan contains both a nitrogen mustard group and an aromatic ring. The nitrogen mustard group is responsible for the alkylation of DNA, while the aromatic ring helps stabilize the molecule, improving its delivery and activity in the body.
The alkylation process involves the formation of covalent bonds between the drug and the DNA bases, particularly guanine. This leads to cross-linking of DNA strands, which blocks transcription and replication, ultimately causing cell death.
Melphalan is particularly effective in treating cancers like multiple myeloma and ovarian cancer because these cancers are highly dependent on rapid cell division, making them more susceptible to the drug's mechanism of action.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Mechanism of Action
Melphalan is an alkylating agent that works by adding alkyl groups to DNA, leading to cross-linking of DNA strands. This cross-linking prevents DNA replication and transcription, ultimately triggering cell death, particularly in rapidly dividing cancer cells. Understanding this mechanism is crucial for appreciating how melphalan targets cancerous tissues.
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General Mechanism
Selectivity for Cancer Cells
Melphalan exhibits selectivity for cancer cells due to their higher proliferation rates compared to normal cells. Cancer cells are more susceptible to DNA damage, making them more likely to be affected by the drug's action. This selectivity helps to minimize damage to normal tissues, although some side effects can still occur.
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Clinical Applications
Melphalan is primarily used in the treatment of multiple myeloma and certain types of ovarian cancer. Its effectiveness in these cancers is supported by clinical studies that demonstrate improved patient outcomes. Understanding its clinical applications helps in evaluating its role in cancer therapy and patient management.
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Related Practice
Textbook Question
Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
b.
605
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Textbook Question
What is the product of each of the following reactions?
c.
d.
893
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Textbook Question
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.)
1239
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Textbook Question
What is the product of each of the following reactions?
g.
962
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Textbook Question
What is the product of each of the following reactions?
a.
869
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