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

1. A Review of General Chemistry

Electronegativity

Organic Chemistry

1. A Review of General Chemistry

Electronegativity

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5:49 minutes

Problem 54b

Textbook Question

In what direction is the dipole moment in calicene? Explain.

Verified step by step guidance

Analyze the structure of calicene: Calicene consists of two aromatic rings connected by a double bond. One ring is a benzene ring, and the other is a cyclopropene ring. The cyclopropene ring has a strained geometry and contributes to the molecule's electronic properties.

Understand the concept of dipole moment: Dipole moment arises due to the separation of charges within a molecule. It depends on the electronegativity differences between atoms and the geometry of the molecule.

Examine the electron distribution: In calicene, the benzene ring is electron-rich due to its aromaticity, while the cyclopropene ring is electron-deficient because of its strained geometry and the presence of the double bond. This creates an electron density imbalance.

Determine the direction of the dipole moment: The dipole moment will point from the electron-rich benzene ring toward the electron-deficient cyclopropene ring. This is because the electron density is higher on the benzene ring, and the dipole moment vector points from negative to positive charge regions.

Summarize the explanation: The dipole moment in calicene is directed from the benzene ring toward the cyclopropene ring due to the difference in electron density and the molecular geometry.

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Key Concepts

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

Dipole Moment

The dipole moment is a vector quantity that measures the separation of positive and negative charges in a molecule. It indicates the direction and strength of the polarity within the molecule, with the arrow pointing from the positive to the negative charge. A molecule with a dipole moment is polar, meaning it has distinct regions of partial positive and negative charge.

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. The shape of a molecule influences its dipole moment, as the spatial distribution of polar bonds can either reinforce or cancel out the overall polarity. In calicene, the unique structure affects how the dipole moment is oriented based on the arrangement of its aromatic rings.

Aromaticity

Aromaticity is a property of cyclic compounds that exhibit resonance stability due to the delocalization of π electrons across the ring structure. In calicene, the presence of aromatic rings contributes to its electronic properties and influences the distribution of electron density, which is crucial for determining the direction of the dipole moment.

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Related Practice

Textbook Question

Use the symbols δ⁺ and δ⁻ to show the direction of the polarity of the indicated bond in each of the following compounds:

e. HO—Br

f. H₃C—Li

Textbook Question

After examining the potential maps for LiH, HF, and H₂, answer the following questions:

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a. Which compounds are polar?

b. Why does LiH have the largest hydrogen?

c. Which compound has the hydrogen that would be most apt to attract a negatively charged molecule?

Textbook Question

Rank the following compounds from highest dipole moment to lowest dipole moment:

Textbook Question

Which of the following compounds have a dipole moment of zero?

Textbook Question

The C=O double bond has a dipole moment of about 2.4 D and a bond length of about 1.23 Å.

a. Calculate the amount of charge separation in this bond.

Textbook Question

1. From what you remember of electronegativities, show the direction of the dipole moments of the following bonds.

2. In each case, predict whether the dipole moment is relatively large (electronegativity difference >0.5) or small.

a. C—Cl

b. C—H

c. C—Li

d. C—N

e. C—O

Textbook Question

For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment

b. cis-1,2-dibromoethene or trans-2,3-dibromobut-2-ene

Textbook Question

For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment.

c. cis-1,2-dibromo-1,2-dichloroethene or cis-1,2-dichloroethene

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