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

Intermolecular Forces

Organic Chemistry

2. Molecular Representations

Intermolecular Forces

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5:32 minutes

Problem 5c,d

Textbook Question

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.
c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene
d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane

Verified step by step guidance

Step 1: Understand the concept of molecular dipole moment. The dipole moment is a measure of the separation of positive and negative charges in a molecule. It depends on both the magnitude of the individual bond dipoles and their spatial arrangement.

Step 2: Analyze the structure of cis-2,3-dibromobut-2-ene. In the cis isomer, the bromine atoms are on the same side of the double bond, which can lead to a net dipole moment as the bond dipoles do not cancel out completely.

Step 3: Analyze the structure of trans-2,3-dibromobut-2-ene. In the trans isomer, the bromine atoms are on opposite sides of the double bond, which often results in the bond dipoles canceling each other out, leading to a lower or zero net dipole moment.

Step 4: Compare the dipole moments of cis-1,2-dichlorocyclobutane and trans-1,3-dichlorocyclobutane. In the cis isomer, the chlorine atoms are on the same side of the cyclobutane ring, which can result in a net dipole moment. In the trans isomer, the chlorine atoms are on opposite sides, which may lead to cancellation of dipole moments.

Step 5: Conclude that the molecular geometry and the relative positions of the substituents (cis vs. trans) significantly affect the net dipole moment. Generally, cis isomers tend to have higher dipole moments than their trans counterparts due to less cancellation of bond dipoles.

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Key Concepts

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

Molecular Dipole Moment

The molecular dipole moment is a measure of the overall polarity of a molecule, determined by the vector sum of all individual bond dipoles. It depends on both the magnitude of the bond dipoles and their spatial arrangement. Molecules with symmetrical arrangements of polar bonds may have a net dipole moment of zero, while asymmetrical arrangements can result in a higher dipole moment.

Cis-Trans Isomerism

Cis-trans isomerism, a type of stereoisomerism, occurs in compounds with restricted rotation around a bond, such as double bonds or in cyclic structures. In cis isomers, similar or identical groups are on the same side, leading to potential dipole moments due to asymmetry. In trans isomers, these groups are on opposite sides, often resulting in cancellation of dipole moments due to symmetry.

Effect of Substituents on Cycloalkanes

In cycloalkanes, the spatial arrangement of substituents significantly affects the molecule's dipole moment. Substituents in a cis configuration can create a net dipole moment due to their additive effect, while in a trans configuration, the dipoles may cancel out. The position and type of substituents, along with the ring strain, influence the overall molecular polarity.

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Textbook Question

Which has

h. the higher boiling point: diethyl ether or butyl alcohol?

Textbook Question

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

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For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

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For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

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Textbook Question

For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?

b. cis- or trans-2,3-dichlorobut-2-ene

Textbook Question

For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?

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Textbook Question

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Textbook Question

a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?

b. Which would you expect to have a higher boiling point?

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For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning. c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane

Key Concepts

Molecular Dipole Moment

Cis-Trans Isomerism

Effect of Substituents on Cycloalkanes

Watch next

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.
c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene
d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane