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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2:48 minutes

Problem 9d

Textbook Question

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.
(d)

Verified step by step guidance

Step 1: Begin by understanding the definitions of the terms hydrophilic, hydrophobic, lipophilic, and lipophobic. Hydrophilic refers to molecules that interact well with water (water-loving), while hydrophobic refers to molecules that repel water (water-fearing). Lipophilic refers to molecules that dissolve well in lipids or fats (fat-loving), and lipophobic refers to molecules that repel lipids or fats (fat-fearing).

Step 2: Examine the structure of the molecule provided in part (d). Look for functional groups or structural features that indicate polarity or non-polarity. Polar groups, such as hydroxyl (-OH), carboxyl (-COOH), or amino (-NH2), tend to make a molecule hydrophilic and lipophobic. Non-polar groups, such as alkyl chains or aromatic rings, tend to make a molecule hydrophobic and lipophilic.

Step 3: Determine the molecule's solubility in water and lipids based on its structure. If the molecule has a high proportion of polar groups, it is likely hydrophilic and lipophobic. If the molecule has a high proportion of non-polar groups, it is likely hydrophobic and lipophilic.

Step 4: Consider the balance between polar and non-polar regions in the molecule. Some molecules may have both hydrophilic and lipophilic properties due to the presence of both polar and non-polar regions. For example, amphiphilic molecules, such as phospholipids, have a hydrophilic head and a lipophilic tail.

Step 5: Assign the two classifications for the molecule based on the analysis above. Ensure that the classifications are consistent with the molecule's structural features and solubility properties.

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Key Concepts

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

Hydrophilicity and Hydrophobicity

Hydrophilicity refers to the affinity of a molecule for water, often due to the presence of polar functional groups that can form hydrogen bonds with water. Conversely, hydrophobicity describes the tendency of nonpolar molecules to repel water, making them insoluble in aqueous environments. Understanding these properties is crucial for predicting how molecules interact in biological systems.

Lipophilicity and Lipophobicity

Lipophilicity indicates a molecule's affinity for lipids or fats, often associated with nonpolar characteristics that allow for solubility in organic solvents. In contrast, lipophobicity describes molecules that do not interact favorably with lipids, typically due to polar or charged groups. These classifications are essential for understanding the behavior of molecules in biological membranes and drug design.

Functional Groups and Molecular Classification

Functional groups are specific groups of atoms within molecules that determine their chemical reactivity and properties. The presence of certain functional groups, such as hydroxyl (-OH) or carboxyl (-COOH), can influence whether a molecule is classified as hydrophilic or hydrophobic, and similarly for lipophilic or lipophobic. Recognizing these groups is vital for accurately classifying and predicting the behavior of organic molecules.