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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Problem 65

Textbook Question

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water?

Verified step by step guidance

Begin by examining the chemical structures of Ansaid and Motrin. Look for functional groups that can interact with water molecules, such as hydroxyl (-OH), carboxyl (-COOH), or amine (-NH2) groups.

Consider the polarity of each molecule. Polar molecules tend to be more soluble in water due to their ability to form hydrogen bonds with water molecules. Identify any polar functional groups in each drug.

Evaluate the overall molecular size and shape. Larger molecules or those with extensive hydrophobic regions may have reduced solubility in water.

Analyze the presence of any ionic groups. Ionic compounds generally have higher solubility in water due to the strong electrostatic interactions with water molecules.

Compare the solubility-enhancing features of each drug. The drug with more polar or ionic groups, or fewer hydrophobic regions, is likely to have greater solubility in water.

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Key Concepts

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

Solubility

Solubility refers to the ability of a substance to dissolve in a solvent, typically water. It is influenced by factors such as temperature, pressure, and the chemical nature of the solute and solvent. In organic chemistry, understanding solubility is crucial for predicting how compounds will behave in biological systems and their effectiveness as drugs.

Nonsteroidal Anti-Inflammatory Drugs (NSAIDs)

NSAIDs are a class of medications that reduce inflammation, pain, and fever. They work by inhibiting enzymes called cyclooxygenases (COX), which are involved in the production of prostaglandins, compounds that mediate inflammation. Knowledge of NSAIDs is essential for understanding their pharmacological properties and therapeutic uses.

Chemical Structure and Polarity

The chemical structure of a compound, including its functional groups and overall polarity, significantly affects its solubility in water. Polar molecules tend to be more soluble in polar solvents like water, while nonpolar molecules are less soluble. Analyzing the structures of Ansaid and Motrin will help determine which has greater solubility based on their polarity.

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Related Practice

Textbook Question

Rank the following molecules from least water soluble to most water soluble. Explain your reasoning.

(b) LiCl

Textbook Question

Which of the following reactions would benefit from micellar technology (Figure 7.10), allowing them to be run in water?

(a)

(b)

(c)

Textbook Question

The effectiveness of a barbiturate as a sedative is related to its ability to penetrate the nonpolar membrane of a cell. Which of the following barbiturates would you expect to be the more effective sedative?

Textbook Question

Explain why amino acids, unlike most amines and carboxylic acids, are insoluble in diethyl ether.

Textbook Question

Why are lower molecular weight alcohols more soluble in water than higher molecular weight alcohols?

Textbook Question

Which has

c. the greater solubility in water: 1-butanol or 1-pentanol?

d. the higher boiling point: 1-hexanol or 1-methoxypentane?

Textbook Question

Rank the following molecules from least water soluble to most water soluble. Explain your reasoning.

(e) CH₃CH₂CH₂CH₂CH₃

Textbook Question

In each pair, (i) choose the compound that is most soluble in water. (ii) Within each pair, which is most soluble in nonpolar solvents?

(a)

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