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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3:46 minutes

Problem 63

Textbook Question

A single bond between two carbons with different hybridizations has a small dipole. What is the direction of the dipole in the indicated bonds?
a.
b.

Verified step by step guidance

Step 1: Analyze the hybridization of the carbon atoms involved in the bonds. In bond (a), the first carbon is sp3 hybridized (CH3 group), and the second carbon is sp2 hybridized (part of the double bond). In bond (b), the first carbon is sp3 hybridized (CH3 group), and the second carbon is sp hybridized (part of the triple bond).

Step 2: Understand the concept of electronegativity and hybridization. Carbon atoms with higher s-character (sp > sp2 > sp3) are more electronegative because the electrons are closer to the nucleus. Therefore, sp hybridized carbons are more electronegative than sp2 hybridized carbons, which are more electronegative than sp3 hybridized carbons.

Step 3: Determine the direction of the dipole based on electronegativity differences. In bond (a), the sp2 hybridized carbon is more electronegative than the sp3 hybridized carbon, so the dipole points toward the sp2 hybridized carbon. In bond (b), the sp hybridized carbon is more electronegative than the sp3 hybridized carbon, so the dipole points toward the sp hybridized carbon.

Step 4: Refer to the image provided. In the image, the arrows indicate the direction of the dipole moment. For bond (a), the arrow points toward the sp2 hybridized carbon (CH═CH2 group). For bond (b), the arrow points toward the sp hybridized carbon (C≡CH group).

Step 5: Summarize the findings. The dipole direction in bond (a) is toward the sp2 hybridized carbon, and in bond (b), it is toward the sp hybridized carbon. This aligns with the concept that higher s-character leads to greater electronegativity and influences the dipole direction.

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Key Concepts

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

Hybridization

Hybridization is the concept that describes the mixing of atomic orbitals to form new hybrid orbitals, which can explain the geometry and bonding properties of molecules. In carbon compounds, common hybridizations include sp3, sp2, and sp, corresponding to single, double, and triple bonds, respectively. Understanding hybridization is crucial for predicting molecular shape and bond angles.

Dipole Moment

A dipole moment occurs when there is a separation of charge within a molecule, resulting from differences in electronegativity between bonded atoms. In the context of carbon compounds, the presence of different hybridizations can lead to unequal sharing of electrons, creating a dipole. The direction of the dipole is from the positive to the negative end, indicating the overall polarity of the bond.

Electronegativity

Electronegativity is a measure of an atom's ability to attract and hold onto electrons in a chemical bond. In carbon compounds, differences in electronegativity between carbon and other atoms (like hydrogen or halogens) can influence the bond's polarity. Understanding electronegativity helps in predicting the direction of dipoles in molecules, as bonds between atoms with different electronegativities will exhibit a dipole moment.

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Related Practice

Textbook Question

Two isomers of 1,2-dichloroethene are known. One has a dipole moment of 2.4 D; the other has zero dipole moment. Draw the two isomers, and explain why one has zero dipole moment.

CHCl=CHCl 1,2-dichloroethene

Textbook Question

1. Draw the Lewis structure.

2. Show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. Estimate whether the compound will have a large, small, or zero dipole moment.

g. HCN

h. CH₃CHO

i. H₂C=NH

Textbook Question

1. Draw the Lewis structure.

2. Show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. Estimate whether the compound will have a large, small, or zero dipole moment.

d. CH₃F

e. CF₄

f. CH₃OH

Textbook Question

Sulfur dioxide has a dipole moment of 1.60 D. Carbon dioxide has a dipole moment of zero, even though C―O bonds are more polar than S―O bonds. Explain this apparent contradiction.

Textbook Question

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

a. CH₃CH=NCH₃

b. CH₃CH₂OH

c. CBr₄

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.

b. Use this information to evaluate the relative importance of the following two resonance contributors:

Textbook Question

The C≡N triple bond in acetonitrile has a dipole moment of about 3.6 D and a bond length of about 1.16 Å. Calculate the amount of charge separation in this bond. How important is the charge-separated resonance form in the structure of acetonitrile?

Textbook Question

For the molecules shown, indicate the direction of the dipole moment.

(b)

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