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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3:26 minutes

Problem 73a

Textbook Question

Which oxygen atom has the greater electron density?

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Identify the functional group in the molecule. The structure contains an ester functional group, which consists of a carbonyl group (C=O) and an alkoxy group (-OCH3).

Examine the two oxygen atoms in the ester group. One oxygen is part of the carbonyl group (C=O), and the other is part of the alkoxy group (-OCH3).

Consider the electron density distribution. The oxygen in the carbonyl group is directly bonded to the carbon atom, which is sp2 hybridized and has a partial positive charge due to the electronegativity difference. This oxygen is involved in resonance with the carbonyl group, which delocalizes its electron density.

Analyze the alkoxy oxygen (-OCH3). This oxygen is bonded to a carbon atom and does not participate in resonance with the carbonyl group. It retains its lone pairs and is less influenced by electron withdrawal compared to the carbonyl oxygen.

Conclude that the alkoxy oxygen (-OCH3) has greater electron density because it is not involved in resonance and is less affected by the electron-withdrawing effects of the carbonyl group.

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Key Concepts

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

Electronegativity

Electronegativity is the tendency of an atom to attract electrons towards itself in a chemical bond. In organic chemistry, oxygen is more electronegative than carbon and hydrogen, which means it pulls electron density towards itself. This property is crucial for understanding the distribution of electron density in molecules, particularly in functional groups containing oxygen.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the context of the given structure, resonance can affect the electron density around the oxygen atoms. The more resonance structures that can be drawn, the more stable the molecule is, and this can influence the electron density on specific atoms, including oxygen.

Inductive Effect

The inductive effect refers to the transmission of charge through a chain of atoms in a molecule due to the electronegativity differences. In the provided structure, the presence of electron-withdrawing groups (like the carbonyl group) can increase the electron density on adjacent atoms, including the oxygen atoms. Understanding this effect is essential for determining which oxygen atom has greater electron density.

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Textbook Question

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

a. ethyl chloride or ethyl iodide

b. 1-bromopropane or cyclopropane

Textbook Question

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

a. cis-1,2-difluoroethene or trans-1,2-difluoroethene

Textbook Question

Which compound has the greater electron density on its oxygen atom?

Textbook Question

Which compound has the greater electron density on its nitrogen atom?

Textbook Question

Refer to the electrostatic potential maps <IMAGE> to answer the following questions:

c. Why is the center of the electrostatic potential map of benzene more red than the center of the electrostatic potential map of pyridine?

Textbook Question

Which is more reactive, an organolithium compound or an organosodium compound? Explain your answer.

Textbook Question

(a) Rank the following bonds in terms of the strength of their bond dipole (1 = weakest, 6 = strongest).

(b) Which carbon has the largest δ⁺ ?

C―F, C―Br, C―I, C―H, C―C, C―Cl

Textbook Question

A mixture of seven amino acids (glycine, glutamate, leucine, lysine, alanine, isoleucine, and aspartate) is separated by chromatography. Explain why only six spots show up when the chromatographic plate is coated with ninhydrin and heated.

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