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

18. Aromaticity

Aromaticity

Organic Chemistry

18. Aromaticity

Aromaticity

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Problem 68

Textbook Question

Molecule A is significantly more water soluble than molecule B. Justify this observation.

Verified step by step guidance

Examine the structures of Molecule A and Molecule B. Molecule A contains two aromatic rings with nitrogen atoms, while Molecule B contains two saturated rings with nitrogen atoms.

Consider the role of aromaticity in solubility. Aromatic rings, like those in Molecule A, can participate in pi-stacking interactions and may also engage in hydrogen bonding with water due to the presence of nitrogen atoms.

Analyze the presence of nitrogen atoms. In Molecule A, the nitrogen atoms are part of aromatic heterocycles, which can enhance solubility through hydrogen bonding with water. In Molecule B, the nitrogen atoms are part of saturated rings, which are less likely to participate in such interactions.

Evaluate the overall polarity of the molecules. Molecule A, with its aromatic rings and nitrogen atoms, is likely more polar than Molecule B, which contributes to its higher water solubility.

Conclude that the increased water solubility of Molecule A is due to its aromatic structure and the presence of nitrogen atoms that can engage in hydrogen bonding, making it more polar and soluble in water compared to Molecule B.

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Key Concepts

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

Polarity

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Molecules with polar bonds have regions of partial positive and negative charges, which allows them to interact favorably with water, a polar solvent. The greater the polarity of a molecule, the more soluble it is in water, as polar molecules tend to dissolve well in polar solvents.

Hydrogen Bonding

Hydrogen bonding is a type of attractive interaction that occurs between a hydrogen atom bonded to a highly electronegative atom (like oxygen or nitrogen) and another electronegative atom. This interaction significantly increases the solubility of a molecule in water, as it allows for the formation of strong attractions between the solute and solvent molecules, facilitating dissolution.

Molecular Structure

The molecular structure of a compound, including its functional groups and overall shape, plays a crucial role in its solubility. For instance, the presence of hydroxyl (-OH) groups can enhance water solubility due to their ability to form hydrogen bonds. Conversely, large hydrophobic regions can hinder solubility in water, making it essential to analyze the structural features of molecules A and B to understand their differing solubility.

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Related Practice

Textbook Question

Using the information in Figure 16-2, calculate the values of ∆H° for the following reactions:

(b)

Textbook Question

Using the information in Figure 16-2, calculate the values of ∆H° for the following reactions:

(c)

Multiple Choice

How does ΔH°_hydr of an aromatic molecule compare to an otherwise identical sample of an analogous nonconjugated molecule?

Textbook Question

Does the MO energy diagram of cyclooctatetraene (Figure 16-8) appear to be a particularly stable or unstable configuration? Explain.

Textbook Question

If Kekulé's original hypothesis had been correct and benzene was really an equilibrium between two structures, how many distinct isomers would exist for 1,2-dichlorobenzene?

Textbook Question

a. Draw the resonance forms of benzene, cyclobutadiene, and cyclooctatetraene, showing all the carbon and hydrogen atoms.

b. Assuming that these molecules are all planar, show how the p orbitals on the sp2 hybrid carbon atoms form continuous rings of overlapping orbitals above and below the plane of the carbon atoms.

Textbook Question

Using the information in Figure 16-2, calculate the values of ∆H° for the following reactions:

(a)

Textbook Question

Using the information in Figure 16-2, calculate the values of ∆H° for the following reactions:

(b)

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