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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4:33 minutes

Problem 29a,b,c

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

Verified step by step guidance

Step 1: For each compound, start by drawing the Lewis structure. Identify the central atom and arrange the surrounding atoms accordingly. Ensure that all atoms satisfy the octet rule, except for hydrogen, which follows the duet rule.

Step 2: For CH3CH=NCH3, draw the Lewis structure with a double bond between the carbon and nitrogen. For CH3CH2OH, draw the Lewis structure with an oxygen atom bonded to the second carbon and a hydrogen atom bonded to the oxygen. For CBr4, draw the Lewis structure with carbon as the central atom and four bromine atoms surrounding it.

Step 3: Identify the bond dipole moments. For CH3CH=NCH3, the C=N bond will have a dipole moment due to the difference in electronegativity between carbon and nitrogen. For CH3CH2OH, the C-O and O-H bonds will have dipole moments. For CBr4, the C-Br bonds will have dipole moments, but they will cancel out due to symmetry.

Step 4: Analyze how these bond dipole moments contribute to the overall molecular dipole moment. For CH3CH=NCH3, the dipole moments may not cancel out, leading to a net dipole moment. For CH3CH2OH, the dipole moments will add up, resulting in a significant molecular dipole moment. For CBr4, the symmetry of the molecule leads to a cancellation of dipole moments, resulting in a zero molecular dipole moment.

Step 5: Estimate the magnitude of the dipole moment for each compound. CH3CH=NCH3 is likely to have a small dipole moment due to partial cancellation of dipoles. CH3CH2OH will have a large dipole moment due to the strong dipole of the O-H bond. CBr4 will have a zero dipole moment due to its symmetrical tetrahedral shape.

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Key Concepts

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

Lewis Structures

Lewis structures are diagrams that represent the bonding between atoms of a molecule and the lone pairs of electrons that may exist. They are essential for visualizing the arrangement of atoms and electrons, helping to predict the geometry and reactivity of the molecule. Understanding how to draw Lewis structures is crucial for analyzing molecular properties such as dipole moments.

Bond Dipole Moments

Bond dipole moments arise from differences in electronegativity between bonded atoms, creating a partial positive and negative charge across the bond. These dipoles can be represented as vectors pointing from the less electronegative atom to the more electronegative atom. Understanding bond dipole moments is key to determining the overall molecular dipole moment, which affects the molecule's polarity and interactions.

Molecular Dipole Moment

The molecular dipole moment is the vector sum of all individual bond dipole moments and any lone pair contributions within a molecule. It indicates the overall polarity of the molecule, influencing properties like solubility and boiling point. Estimating the molecular dipole moment involves assessing the symmetry and arrangement of dipoles, which can result in a large, small, or zero dipole moment.

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Related Practice

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

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

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)

Textbook Question

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

(a)

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