Organic Chemistry
John McMurry
9th Edition
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,Table of Contents
1. Structure and Bonding
2. Polar Covalent Bonds; Acids and Bases
3. Organic Compounds: Alkanes and Their Stereochemistry
4. Organic Compounds: Cycloalkanes and Their Stereochemistry
5. Stereochemistry at Tetrahedral Centers
6. An Overview of Organic Reactions
7. Alkenes: Structure and Reactivity
8. Alkenes: Reactions and Synthesis
9. Alkynes: An Introduction to Organic Synthesis
10. Organohalides
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy
13. Structure Determination: Nuclear Magnetic Resonance Spectroscopy
14. Conjugated Compounds and Ultraviolet Spectroscopy
15. Benzene and Aromaticity
16. Chemistry of Benzene: Electrophilic Aromatic Substitution
17. Alcohols and Phenols
18. Ethers and Epoxides; Thiols and Sulfides
19. Aldehydes and Ketones: Nucleophilic Addition Reactions
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20. Carboxylic Acids and Nitriles
21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
22. Carbonyl Alpha-Substitution Reactions
23. Carbonyl Condensation Reactions
24. Amines and Heterocycles
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25. Biomolecules: Carbohydrates
26. Biomolecules: Amino Acids, Peptides, and Proteins
27. Biomolecules: Lipids
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28. Biomolecules: Nucleic Acids
29. The Organic Chemistry of Metabolic Pathways
30. Orbitals and Organic Chemistry: Pericyclic Reactions
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31. Synthetic Polymers
Appendices
• Appendix A: Nomenclature of Polyfunctional Organic Compounds
• Appendix B: Acidity Constants for Some Organic Compounds
• Appendix C: Glossary
• Appendix D: Answers to In-Text Problems
,Chapter 01 - Structure and Bonding
1. Give the ground-state electron configuration for carbon (atomic number 6).
ANSWER: 1s22s22px12py1 or 1s22s22p2
POINTS: 1
2. Give the ground-state electron configuration for fluorine (atomic number 9).
ANSWER: 1s22s22px2 2py2 2pz1 or 1s22s22p5
POINTS: 1
3. Give the ground-state electron configuration for magnesium (atomic number 12).
ANSWER: 1s22s22p63s2
POINTS: 1
4. How many electrons does silicon have in its valence shell?
ANSWER: four
POINTS: 1
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Exhibit 1-1
Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and show all non-bonding
electrons.
5. C2Cl4 tetrachloroethylene
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ANSWER:
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POINTS: 1
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6. CO2 carbon dioxide
ANSWER:
POINTS: 1
7. CH4O methanol
ANSWER:
POINTS: 1
Exhibit 1-2
Consider the structure of urea, shown below, to answer the following question(s).
8. Refer to Exhibit 1-2. Fill in any non-bonding valence electrons that are missing from the line-bond structure.
, ANSWER:
POINTS: 1
9. Refer to Exhibit 1-2. The carbon atom in urea is:
a. sp3 hybridized
b. sp2 hybridized
c. sp hybridized
d. not hybridized
ANSWER: b
POINTS: 1
10. Refer to Exhibit 1-2. The predicted NH2−C=O bond angle in urea is:
a. 109.5°
b. 120°
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c. 180°
d. not predictable
ANSWER: b
POINTS: 1
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Exhibit 1-3
Determine the hybridization for the indicated atoms in each structure below.
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11. Refer to Exhibit 1-3. The hybridization of this oxygen atom (A) is .
ANSWER: sp2
POINTS: 1
12. Refer to Exhibit 1-3. The hybridization of this oxygen atom (B) is .
ANSWER: sp3
POINTS: 1
13. Refer to Exhibit 1-3. The hybridization of this carbon atom (C) is .
ANSWER: sp3
POINTS: 1
14. Refer to Exhibit 1-3. The hybridization of this carbon atom (D) is .
ANSWER: sp
POINTS: 1