TEST BANK
Organic Chemistry Mechanistic Patterns, 2ND Edition
by Ogilvie, Ackroyd, All Chapter 1 - 20
,TABLE OF CONTENTS
1. CHAPTER 1 Carbon and Its Compounds
2. CHAPTER 2 Anatomy of an Organic Molecule
3. CHAPTER 3 Molecules in Motion: Conformations by Rotations
4. CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules
5. CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms
6. CHAPTER 6 Acids and Bases
7. CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups
8. CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols
9. CHAPTER 9 Conjugation and Aromaticity
10. CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed
Orth
11. CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions
12. CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions
13. CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy
14. CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy
15. CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives
16. CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds
17. CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions
18. CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and
19. CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions
20. CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cy
,CHAPTER 1 - Carbon and Its Compounds
2-
1. Which of the following represents the ground state electron configuration for ion?
a O
a. 1s22s22p4
b. 1s22s22p2
c. 1s22s22p6
d. 2s22p4
ANSWER: c
2. How many valence electrons does a nitrogen atom contain?
a. 2
b. 3
c. 5
d. 7
ANSWER: c
2-
O ion contain?
3. How many valence electrons does an
a. 2
b. 6
c. 8
d. 10
ANSWER: c
4. What is the Lewis structure of a compound that has the formula of CCl3 and contains 24 valence
electrons?
a.
b.
c.
d.
,ANSWER: d
5. How many bonded and non-bonded electrons does a molecule with no formal charges and the
formula C2H4O2 contain?
a. 4 bonded, 4 non-bonded
b. 7 bonded. 4 non-bonded
c. 7 bonded, 5 non-bonded
d. 4 bonded, 7 non-bonded
ANSWER: b
Figure 1
6. Referring to Figure 1, what is the formal charge of the oxygen atom at I?
a. +1
b. 0
c. -1
d. -2
ANSWER: b
7. Referring to Figure 1, what is the formal charge of the oxygen atom at II?
a. +1
b. 0
c. -1
d. -2
ANSWER: c
8. Referring to Figure 1, what is the formal charge of the oxygen atom at III?
a. +1
b. 0
c. -1
d. -2
ANSWER: a
9. What best represents a C-H bond in CH4?
a. s-sp3 orbital overlap
, b. sp3-sp3 orbital overlap
c. s-s orbital overlap
d. p-p orbital overlap
ANSWER: a
10. What best represents the C-C bond in C2H6?
a. s-sp3 orbital overlap
b. sp3-sp3 orbital overlap
c. s-s orbital overlap
d. p-p orbital overlap
ANSWER: b
Figure 2
The following questions refer to the structure of heroin (shown below).
11. Referring to Figure 2, what is the hybridization of the nitrogen atom?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: d
12. Referring to Figure 2, what is the geometry of the carbon atom shown at I?
a. bent
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: b
13. Referring to Figure 2, what is the geometry of the carbon atom shown at II?
a. bent
b. trigonal planar
, c. tetrahedral
d. trigonal pyramidal
ANSWER: c
14. Referring to Figure 2, what is the hybridization of the carbon atom at I?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: c
15. Referring to Figure 2, what is the hybridization of the carbon atom at II?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: d
6 2 4
2 2
16. Which element or ion has the following electron configuration: 1s 2s 2p 3s 3s ?
a. S
b. O
c. Ar
d. Si
ANSWER: a
17. How many orientations exist for a s orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER: a
18. How many orientations exist for a p orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER: c
19. How many orientations exist for sp
a a. 1
3
,orbital?
, b. 2
c. 3
d. 4
ANSWER:
d
20. How many orientations exist for an sp orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER:
b
21. What is the geometry around an
sp hybridized carbon?
2
a. linear
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: b
22. What is the geometry around an sp hybridized carbon?
a. linear
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: a
23. How many bonds does oxygen make while remaining neutral?
a. 1
b. 2
c. 3
d. 4
ANSWER: b
24. How many hydrogens does the following line structure contain?
a. 1
Organic Chemistry Mechanistic Patterns, 2ND Edition
by Ogilvie, Ackroyd, All Chapter 1 - 20
,TABLE OF CONTENTS
1. CHAPTER 1 Carbon and Its Compounds
2. CHAPTER 2 Anatomy of an Organic Molecule
3. CHAPTER 3 Molecules in Motion: Conformations by Rotations
4. CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules
5. CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms
6. CHAPTER 6 Acids and Bases
7. CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups
8. CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols
9. CHAPTER 9 Conjugation and Aromaticity
10. CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed
Orth
11. CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions
12. CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions
13. CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy
14. CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy
15. CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives
16. CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds
17. CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions
18. CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and
19. CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions
20. CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cy
,CHAPTER 1 - Carbon and Its Compounds
2-
1. Which of the following represents the ground state electron configuration for ion?
a O
a. 1s22s22p4
b. 1s22s22p2
c. 1s22s22p6
d. 2s22p4
ANSWER: c
2. How many valence electrons does a nitrogen atom contain?
a. 2
b. 3
c. 5
d. 7
ANSWER: c
2-
O ion contain?
3. How many valence electrons does an
a. 2
b. 6
c. 8
d. 10
ANSWER: c
4. What is the Lewis structure of a compound that has the formula of CCl3 and contains 24 valence
electrons?
a.
b.
c.
d.
,ANSWER: d
5. How many bonded and non-bonded electrons does a molecule with no formal charges and the
formula C2H4O2 contain?
a. 4 bonded, 4 non-bonded
b. 7 bonded. 4 non-bonded
c. 7 bonded, 5 non-bonded
d. 4 bonded, 7 non-bonded
ANSWER: b
Figure 1
6. Referring to Figure 1, what is the formal charge of the oxygen atom at I?
a. +1
b. 0
c. -1
d. -2
ANSWER: b
7. Referring to Figure 1, what is the formal charge of the oxygen atom at II?
a. +1
b. 0
c. -1
d. -2
ANSWER: c
8. Referring to Figure 1, what is the formal charge of the oxygen atom at III?
a. +1
b. 0
c. -1
d. -2
ANSWER: a
9. What best represents a C-H bond in CH4?
a. s-sp3 orbital overlap
, b. sp3-sp3 orbital overlap
c. s-s orbital overlap
d. p-p orbital overlap
ANSWER: a
10. What best represents the C-C bond in C2H6?
a. s-sp3 orbital overlap
b. sp3-sp3 orbital overlap
c. s-s orbital overlap
d. p-p orbital overlap
ANSWER: b
Figure 2
The following questions refer to the structure of heroin (shown below).
11. Referring to Figure 2, what is the hybridization of the nitrogen atom?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: d
12. Referring to Figure 2, what is the geometry of the carbon atom shown at I?
a. bent
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: b
13. Referring to Figure 2, what is the geometry of the carbon atom shown at II?
a. bent
b. trigonal planar
, c. tetrahedral
d. trigonal pyramidal
ANSWER: c
14. Referring to Figure 2, what is the hybridization of the carbon atom at I?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: c
15. Referring to Figure 2, what is the hybridization of the carbon atom at II?
a. p
b. sp
2
c. sp
3
d. sp
ANSWER: d
6 2 4
2 2
16. Which element or ion has the following electron configuration: 1s 2s 2p 3s 3s ?
a. S
b. O
c. Ar
d. Si
ANSWER: a
17. How many orientations exist for a s orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER: a
18. How many orientations exist for a p orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER: c
19. How many orientations exist for sp
a a. 1
3
,orbital?
, b. 2
c. 3
d. 4
ANSWER:
d
20. How many orientations exist for an sp orbital?
a. 1
b. 2
c. 3
d. 4
ANSWER:
b
21. What is the geometry around an
sp hybridized carbon?
2
a. linear
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: b
22. What is the geometry around an sp hybridized carbon?
a. linear
b. trigonal planar
c. tetrahedral
d. trigonal pyramidal
ANSWER: a
23. How many bonds does oxygen make while remaining neutral?
a. 1
b. 2
c. 3
d. 4
ANSWER: b
24. How many hydrogens does the following line structure contain?
a. 1
