Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

8. Elimination Reactions

Cumulative Substitution/Elimination

Organic Chemistry

8. Elimination Reactions

Cumulative Substitution/Elimination

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7:04 minutes

Problem 52

Textbook Question

Why is melphalan a good cancer drug?

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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.

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.

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

Would you expect the following bases to favor E1 or E2 elimination?

(d) H₂O

Textbook Question

Paying close attention to the stereochemical outcome, predict the product of these elimination reactions.

(c)

Textbook Question

Indicate the type of catalysis that is occurring in the slow step in each of the following reaction sequences:

Textbook Question

Indicate the type of catalysis that is occurring in the slow step in each of the following reaction sequences:

Textbook Question

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

c. Cl⁻ or Br⁻

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.)

Textbook Question

Finish Solved Problem 7-3 by showing how the rearranged carbocations give the four products shown in the problem. Be careful when using curved arrows to show deprotonation and/or nucleophilic attack by the solvent. The curved arrows always show movement of electrons, not movement of protons or other species.

Textbook Question

Give the substitution and elimination products you would expect from the following reactions.

c. 1-bromo-2-methylcyclohexane + silver nitrate in water (AgNO₃ forces ionization)

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