Organic Chemistry
John E. McMurry
8th Edition
JN
U
R
SE
1
, 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
JN
13. Structure Determination: Nuclear Magnetic Resonance Spectroscopy
14. Conjugated Compounds and Ultraviolet Spectroscopy
15. Benzene and Aromaticity
16. Chemistry of Benzene: Electrophilic Aromatic Substitution
U
17. Alcohols and Phenols
18. Ethers and Epoxides; Thiols and Sulfides
R
19. Aldehydes and Ketones: Nucleophilic Addition Reactions
20. Carboxylic Acids and Nitriles
21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
SE
22. Carbonyl α-Substitution Reactions
23. Carbonyl Condensation Reactions
24. Amines and Heterocycles
25. Biomolecules: Carbohydrates
26. Biomolecules: Amino Acids, Peptides, and Proteins
27. Biomolecules: Lipids
28. Biomolecules: Nucleic Acids
29. The Organic Chemistry of Metabolic Pathways
30. Orbitals and Organic Chemistry: Pericyclic Reactions
31. Synthetic Polymers
2
,Chapter 1—Structure and Bonding
SHORT ANSWER
1. Give the ground-state electron configuration for carbon (atomic number 6).
ANS:
1s22s22px12py1 or 1s22s22p2
2. Give the ground-state electron configuration for fluorine (atomic number 9).
ANS:
1s22s22px2 2py2 2pz1 or 1s22s22p5
3. Give the ground-state electron configuration for magnesium (atomic number 12).
JN
ANS:
1s22s22p63s2
4. How many electrons does silicon have in its valence shell?
U
ANS:
four
R
Exhibit 1-1
Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and show
SE
all non-bonding electrons.
5. C2Cl4 tetrachloroethylene
ANS:
6. CO2 carbon dioxide
ANS:
7. CH4O methanol
3
, Structure and Bonding
ANS:
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.
ANS:
JN
9. Refer to Exhibit 1-2. The carbon atom in urea is:
U
sp3 hybridized
sp2 hybridized
sp hybridized
R
not hybridized
ANS:
SE
b
10. Refer to Exhibit 1-2. The predicted NH2-C=O bond angle in urea is:
109.5
120
180
not predictable
ANS:
b
4