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

2. Molecular Representations

How To Determine Solubility

Organic Chemistry

2. Molecular Representations

How To Determine Solubility

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5:01 minutes

Problem 2

Textbook Question

Methoxychlor is an insecticide that was intended to take DDT’s place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned—in 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?

Verified step by step guidance

Analyze the structure of methoxychlor: It contains two aromatic rings, each substituted with a methoxy group (-OCH3), and a central carbon bonded to three chlorine atoms.

Compare methoxychlor to DDT: DDT has two aromatic rings without methoxy groups and a central carbon bonded to three chlorine atoms. The absence of polar functional groups in DDT makes it highly hydrophobic and more soluble in fatty tissues.

Understand the role of methoxy groups: The methoxy groups (-OCH3) in methoxychlor introduce polarity to the molecule due to the electronegativity of oxygen. This increases its ability to interact with polar solvents like water and decreases its hydrophobicity.

Explain solubility in fatty tissues: Fatty tissues are nonpolar environments, favoring the solubility of nonpolar molecules like DDT. Methoxychlor, being more polar due to the methoxy groups, is less compatible with nonpolar fatty tissues.

Conclude why methoxychlor is less soluble: The increased polarity from the methoxy groups reduces methoxychlor's solubility in fatty tissues compared to DDT, which lacks these polar functional groups.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrophobicity and Lipophilicity

Hydrophobicity refers to the tendency of a compound to repel water, while lipophilicity indicates its affinity for fats and oils. Compounds that are more lipophilic tend to accumulate in fatty tissues. Methoxychlor's lower lipophilicity compared to DDT means it is less likely to dissolve in fatty tissues, leading to reduced bioaccumulation.

Chemical Structure and Functional Groups

The chemical structure of a compound, including its functional groups, significantly influences its solubility properties. Methoxychlor has a different arrangement of functional groups compared to DDT, which affects its interaction with lipid membranes and its overall solubility in fatty tissues.

Biodegradability

Biodegradability refers to the ability of a substance to be broken down by biological organisms, such as bacteria. Methoxychlor is designed to be more readily biodegradable than DDT, which contributes to its lower environmental persistence and accumulation in living organisms, making it a more favorable alternative despite its eventual ban.