浙江大学有机化学乙 exercise 1
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at are the formal charges of boron and nitrogen, respectively, in the following structure?
a. b. c. d.
-1 and +1 -1 and 0 0 and +1 0 and 0
25. Which one of the following species is formed when diazomethane loses a nitrogen molecule?
19. Predict which bond is the most polar in ethanol, CH3CH2OH? a. C-C b. C-H c. C-O d. O-H 15. What is the formal charge on the carbon atom?
a. b. C d.
a. b. c. d. 3
anti gauche skewed eclipsed What is the dihedral (torsion) angle between the two bromine atoms in the following sawhorse drawing?
a. b. c. d. 4
1
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
5
Identify the spatial relationship of the two chlorine atoms.
a. b. c. d. 6
gauche anti eclipsed twist Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?
a. b. c. d.
A is more stable. B is more stable. A and B are equal in stabilities. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
23. Which of the following molecules would you expect to have a dipole moment? I. CO2 a. b. c. d. II and III only II only III I, II, and III II. HCN III. CHCl3
10 The correct IUPAC name of the following compound is:
a. b. c. d.
2-ethyl-3,5-dimethylheptane 6-ethyl-5,5-dimethylheptane 3,4,4-trimethyloctane 5,5,6-trimethyloctane
a. b. c. d.
A B C D
2
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
9. The IUPAC name of the following compound is:
a. b. c. d.
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane 1,1-dimethylcyclohexane cis-1,3-dimethylcyclohexane
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
1
What is the IUPAC name of the compound shown below?
a. 1,2,3-trimethylbutane b. .2,3-dimethylpentane c. 2,3,4-trimethylpentane d. 2-isopropylbutane 2 Identify the conformation of butane shown below.
7. Identify the two atoms anti to the bromine.
a. b. c. d 8
the equatorial H's on C-2 and C-6 the axial H's on C-2 and C-6 C-2 and C-6 C-3 and C-5 Which isomer of 1-tert-butyl-3-ethyl-5-methylcyclohexane below is thermodynamically the most stable?
diazomethane
a. A
6
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
b. B c. C d. D 41. Which statement correctly describes the structures of BH3 and NH3? a. Both are trigonal and planar. b. Both are pyramidal. c. BH3 is trigonal planar and NH3 is trigonal pyramidal. d. BH3 is trigonal pyramidal and NH3 is trigonal planar. 45. Which one of the following is the strongest base?
b. 0, -1 c. +1, 0 d. 0, 0 22. Based on VSEPR theory, which of the following species has (have) a trigonal pyramidal geometry? I. CO32¯ a. b. c. d. only I only II I and II II and III II. NH3 III. CH3+
a. b. c. d.
I, II, and III I, III, and IV only I and III all are constitutional isomers
15 Arrange the following isomeric alkanes in order of increasing boiling point. I. n-heptane II. 2,3-dimethylpentane III. 2,2,3-trimethylbutane I < II < III II < III < I III < I < II III < II < I
+1 0 -1 -2
20. Which of the following describes the relationship between the following two structures?
a. b. c. d.
identical structures resonance forms constitutional isomers different compounds with different compositions
12. What is the IUPAC name of the following?
a. b. c. d.
1-ethyl-4.4-dimethylcyclopentane 1-ethyl-3,3-dimethylcyclopentane 3-ethyl-1,1-dimethylcyclopentane 4-ethyl-1,1-dimethylcyclopentane
A b. c. d.
6-isopropyl-3-methylnonane 6-propyl-3-methylnonane 2-ethyl-5-isopropyloctane 2-ethyl-5-propyloctane
4
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
21 The formal charges on the nitrogen and oxygen in the following structures are, respectively:
a. +1, -1
5
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
18.
The reaction of acetylene with hydrogen gas is shown below. Which statements are true concerning the reaction?
I. Acetylene is oxidized to ethane. II. Acetylene is reduced to ethane. III. Carbon changes oxidation state from -1 to -3. IV. Hydrogen (from H2) changes oxidation state from 0 to +1. a. b. c. d. I and III II and IV I, III, and IV II, III, and IV
a. b. c. d.
A B C D
7
0o 30o 60o 90o Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?
a. b. c. d.
A is more stable. B is more stable. A and B are equal in stabilities. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
13. The correct IUPAC name of the following compound is:
a. (1-methylhexyl)cyclopentane
3
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
b. (1-pentylethyl)cyclopentane c. 2-cyclopentylheptane d. 1-cyclopentyl-2-heptane 14 Which of the following are constitutional isomers?
a. b. c. d.
16. Which of the following has(have) a higher oxidation state of carbon than the carbon in formaldehyde, H2C=O? I. CH3OH II. HCO2H III. H2CO3 a. I b. III c. II and III d. I, II, and III 17 What is the IUPAC name of the following?
11. The correct IUPAC name of the following is:
a. b. c. d.
2,4,7-trimethylnonane 3,6,8-trimethylnonane 7-ethyl-2,4-dimethyloctane 2-ethyl-5,7-dimethyloctane
a. b. c. d.
-1 and +1 -1 and 0 0 and +1 0 and 0
25. Which one of the following species is formed when diazomethane loses a nitrogen molecule?
19. Predict which bond is the most polar in ethanol, CH3CH2OH? a. C-C b. C-H c. C-O d. O-H 15. What is the formal charge on the carbon atom?
a. b. C d.
a. b. c. d. 3
anti gauche skewed eclipsed What is the dihedral (torsion) angle between the two bromine atoms in the following sawhorse drawing?
a. b. c. d. 4
1
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
5
Identify the spatial relationship of the two chlorine atoms.
a. b. c. d. 6
gauche anti eclipsed twist Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?
a. b. c. d.
A is more stable. B is more stable. A and B are equal in stabilities. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
23. Which of the following molecules would you expect to have a dipole moment? I. CO2 a. b. c. d. II and III only II only III I, II, and III II. HCN III. CHCl3
10 The correct IUPAC name of the following compound is:
a. b. c. d.
2-ethyl-3,5-dimethylheptane 6-ethyl-5,5-dimethylheptane 3,4,4-trimethyloctane 5,5,6-trimethyloctane
a. b. c. d.
A B C D
2
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
9. The IUPAC name of the following compound is:
a. b. c. d.
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane 1,1-dimethylcyclohexane cis-1,3-dimethylcyclohexane
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
1
What is the IUPAC name of the compound shown below?
a. 1,2,3-trimethylbutane b. .2,3-dimethylpentane c. 2,3,4-trimethylpentane d. 2-isopropylbutane 2 Identify the conformation of butane shown below.
7. Identify the two atoms anti to the bromine.
a. b. c. d 8
the equatorial H's on C-2 and C-6 the axial H's on C-2 and C-6 C-2 and C-6 C-3 and C-5 Which isomer of 1-tert-butyl-3-ethyl-5-methylcyclohexane below is thermodynamically the most stable?
diazomethane
a. A
6
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
b. B c. C d. D 41. Which statement correctly describes the structures of BH3 and NH3? a. Both are trigonal and planar. b. Both are pyramidal. c. BH3 is trigonal planar and NH3 is trigonal pyramidal. d. BH3 is trigonal pyramidal and NH3 is trigonal planar. 45. Which one of the following is the strongest base?
b. 0, -1 c. +1, 0 d. 0, 0 22. Based on VSEPR theory, which of the following species has (have) a trigonal pyramidal geometry? I. CO32¯ a. b. c. d. only I only II I and II II and III II. NH3 III. CH3+
a. b. c. d.
I, II, and III I, III, and IV only I and III all are constitutional isomers
15 Arrange the following isomeric alkanes in order of increasing boiling point. I. n-heptane II. 2,3-dimethylpentane III. 2,2,3-trimethylbutane I < II < III II < III < I III < I < II III < II < I
+1 0 -1 -2
20. Which of the following describes the relationship between the following two structures?
a. b. c. d.
identical structures resonance forms constitutional isomers different compounds with different compositions
12. What is the IUPAC name of the following?
a. b. c. d.
1-ethyl-4.4-dimethylcyclopentane 1-ethyl-3,3-dimethylcyclopentane 3-ethyl-1,1-dimethylcyclopentane 4-ethyl-1,1-dimethylcyclopentane
A b. c. d.
6-isopropyl-3-methylnonane 6-propyl-3-methylnonane 2-ethyl-5-isopropyloctane 2-ethyl-5-propyloctane
4
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
21 The formal charges on the nitrogen and oxygen in the following structures are, respectively:
a. +1, -1
5
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
18.
The reaction of acetylene with hydrogen gas is shown below. Which statements are true concerning the reaction?
I. Acetylene is oxidized to ethane. II. Acetylene is reduced to ethane. III. Carbon changes oxidation state from -1 to -3. IV. Hydrogen (from H2) changes oxidation state from 0 to +1. a. b. c. d. I and III II and IV I, III, and IV II, III, and IV
a. b. c. d.
A B C D
7
0o 30o 60o 90o Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?
a. b. c. d.
A is more stable. B is more stable. A and B are equal in stabilities. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
13. The correct IUPAC name of the following compound is:
a. (1-methylhexyl)cyclopentane
3
Organic Chemistry 2007-8 Exercise 1 Date (21/9)
b. (1-pentylethyl)cyclopentane c. 2-cyclopentylheptane d. 1-cyclopentyl-2-heptane 14 Which of the following are constitutional isomers?
a. b. c. d.
16. Which of the following has(have) a higher oxidation state of carbon than the carbon in formaldehyde, H2C=O? I. CH3OH II. HCO2H III. H2CO3 a. I b. III c. II and III d. I, II, and III 17 What is the IUPAC name of the following?
11. The correct IUPAC name of the following is:
a. b. c. d.
2,4,7-trimethylnonane 3,6,8-trimethylnonane 7-ethyl-2,4-dimethyloctane 2-ethyl-5,7-dimethyloctane