CHM 220 Alkanes and Cycloalkanes
Nomenclature and Structure
1. Which of the following is not an IUPAC name for an isomer having the formula C4H9Br?
(A)
1-bromobutane
(B)
1-bromo-2-methylpropane
(C)
2-bromobutane
(D)
1-bromo-3-methylpropane
2. What is the IUPAC name for the compound having the following structure?
Cl
(A)
2-methyl-3-chloropentane
(B)
2-methyl-3-chlorobutane
(C)
1,1-dimethyl-2-chloropropane
(D)
2-chloro-3-methylbutane
3. What is the IUPAC name for the compound having the following structure?
(A)
2,2-diethylbutane
(B)
2,2,2-triethylethane
(C)
3-methyl-3-ethylpentane
(D)
3-ethyl-3-methylpentane
4. Which of the following structures have the correct names?
Cl
1. tert-butyl chloride
Cl
Cl
2. isobutyl chloride
3. sec-butyl chloride
(A)
1 and 2
(B)
2 and 3
(C)
3 and 4
(D)
1 and 4
Cl
4. n-butyl chloride
5. Which of the following structures have the correct names?
(H3C)3C OH
1. tert-butyl alcohol
OH
OH
3. isobutyl alcohol
2. sec-butyl alcohol
(A)
1 and 2
(B)
1 and 3
(C)
2 and 4
(D)
3 and 4
6. What is the correct IUPAC name for the following structure?
H3C
CH3
(A)
1,2-dimethylcyclobutane
(B)
1,3-dimethylcyclobutane
(C)
1,4-dimethylcyclobutane
(D)1,3-dimethylbicyclo[1.1.0]butane
OH
4. butane-3-ol
7. What is the correct IUPAC name for the following structure?
(A)
bicyclo[2.1.0]hexane
(B)
bicyclo[2.2.1]hexane
(C)
bicyclo[2.2.0]hexane
(D)
bicyclo[3.1.0]hexane
8. What is the correct IUPAC name for the following structure?
(A)
bicyclo[2.1.1]hexane
(B)
bicyclo[2.2.1]hexane
(C)
bicyclo[2.2.0]hexane
(D)
bicyclo[3.1.0]hexane
9. Which of the following is a secondary alcohol having the molecular structure C4H10?
A (CH3)2CHCH 2OH
B CH3CH2CHOHCH 3
(A)
A
(B)
B
(C)
C
(D)
D
C
D (CH3)2CHOH
OH
10. Which of the following is a primary alcohol having the molecular formula C4H8O?
A
OH
OH
B
C
D
OH
OH
(A)
A
(B)
B
(C)
C
(D)
D
11. What is the correct formula for isobutylbromide?
(A)
CH3CH2CH2CH(Br)CH3
(B)
(CH3)2CHCH2Br
(C)
Br(CH3)CHCH2CH3
(D)
(CH3)2CHCH2CH2Br
12. How many branched-chain isomers are there of C6H14?
(A)
2
(B)
3
(C)
4
(D)
6
13. How many total isomers are there for dimethylcyclopentane (include cis, trans)?
(A)
3
(B)
5
(C)
7
(D)
9
14. How many isomeric alkanes are there that have the molecular formula C6H14?
(A)
3
(B)
5
(C)
6
(D)
7
15. Which of the following is not a conformer of C5H12?
H
CH3
H
H
C2H5
H
H
H
C2H5
CH3
A
B
H
H3C
H
H
H
CH3
H
CH3
C
H3C H
H
H
H3C
H
D
16. Which of the following is a conformer of isobutane?
H
H3C
H
H5C2
CH3
H
H
H
H
H3C
H
H
CH3
H
H
H
H
CH3
H
H
H
H
CH3
CH3
A
B
C
D
17. Which of the following are gauche forms?
H3C
CH3
H
H
H
H
H
CH3
H
H
H
H3C
H
CH3
H
H
H
H
CH3
H
H
1
2
3
4
1 and 4
(B)
2 and 3
(C)
2 and 4
(D)
3 and 5
H
H
H
H3C
CH3
H
(A)
H3C H
CH3
5
18. Which of the following are anti forms?
H3C
CH3
H
H
H
H
H
CH3
H
H
H
H3C
H
CH3
H
H
H
H
CH3
H
H
1
2
3
4
1 and 4
(B)
2 and 3
(C)
2 and 4
(D)
3 and 5
H
H
H
H3C
CH3
H
(A)
H3C H
CH3
5
19. Which of the following conformers has the highest energy?
H3C H
H3C CH3
CH3
H
H
H
A
HH
H
H
H
H
H CH3
CH3
H
H3C
H
B
C
CH3
H
H
H
D
20. Arrange the conformers of 2,3-dimethylbutane in order of increasing stability (least stable to most stable).
H3C
CH3
H3C
CH3
H
H
1
H3C CH3
H3C
CH3
H
H3C
H
CH3
H
H
CH3
CH3
3
(A)
1, 2, 4, 3
2
(B)
4, 1, 3, 2
(C)
2, 4, 3, 1
(D)
4, 2, 1, 3
H3C CH3
CH3
CH3
H
H
4
21. For methylcyclohexane, the axial conformer is less stable than the equatorial because of which of the
following gauche interactions?
(A)
one methyl-methlyene
(B)
two methyl-methylene
(C)
one methyl-methyl
(D)
two methyl-methyl
22. How many methyl-methylene gauche interactions are there for trans-1,3-dimethylcyclohexane?
(A)
1
(B)
2
(C)
3
(D)
4
23. How many methyl-methylene gauche interactions are there for 1,1-dimethylcyclohexane?
(A)
1
(B)
2
(C)
3
(D)
4
24. Which of the following is the most stable chair form of trans-1-isopropyl-3-methylcyclohexane?
(A) axial isopropyl, equatorial methyl
(B) axial isopropyl, axial methyl
(C) equatorial isopropyl, axial methyl
(D) equatorial isopropyl, equatorial methyl
25. How many cis isomers are there for dimethylcyclobutane?
(A)
1
(B)
2
(C)
3
(D)
4
26. How many trans isomers are there for dimethylcyclopentane?
(A)
1
(B)
2
(C)
3
(D)
4
27. Whcih of the conformations of cyclohexane is most stable?
(A)
boat
(B)
chair
(C)
twist boat
(D)
planar
28. What is the order of increasing energy for the different conformers of cyclohexane (most stable first).
1. Boat
2. Chair
3. Twist boat
(A)
1, 3, 4, 2
(B)
4, 3, 1, 2
(C)
2, 3, 1, 4
(D)
2, 1, 4, 3
4. Planar
29. Which of the following are more stable? (most stable from each pair of compounds)
cis- or trans-1,4-dimethylcyclohexane
cis- or trans-1,3-dimethylcyclohexane
(A)
cis, cis
(B)
cis, trans
(C)
trans, cis
(D)
trans, trans
30. Which of the following are more stable? (most stable from each pair of compounds)
cis- or trans-1,2-dimethylcyclohexane
cis- or trans-1,3-dimethylcyclohexane
(A)
cis, cis
(B)
cis, trans
(C)
trans, cis
(D)
trans, trans
31. In the most stable conformation of trans-1,4-dimethylcyclohexane, what positions do the methyl groups
occupy?
(A)
axial, axial
(B)
equatorial, axial
(C)
equatorial, equatorial
(D)
axial, equatorial
32. In the most stable conformation of cis-1-ethyl-2-methylcyclohexane, what positions do the ethyl and methyl
groups occupy respectively?
(A)
axial, axial
(B)
equatorial, axial
(C)
equatorial, equatorial
(D)
axial, equatorial
33. Which of the following positions is the bridgehead carbon atom?
A
D
B
C
(A)
A
(B)
B
(C)
C
(D)
D
34. Whcih isomer of dimethylbicyclo[2.2.2]octane can have cis and trans forms?
(A)
1,2
(B)
2,3
(C)
1,3
(D)
1,4
Properties and Reactions
35. What is the order of increasing boiling point (lowest first) for the following forms of pentane?
1
2
3
(A)
3, 2, 1, 4
(B)
4, 2, 3, 1
(C)
1, 2, 3, 4
(D)
3, 4, 2, 1
4
36. Which fuel gives the highest heat upon combustion (per mole)?
(A)
natural gas
(B)
gasoline
(C)
LPG (liquid propane)
(D)
all are the same
37. Which of the following contribute most to the strain in cyclopentane?
(A)
eclipsed hydrogen atoms
(B)
bent bonds or angle strain
(C)
all of the other reasons
(D)
transannular non-bonded interaction
38. Arrange the following attractive forces in order of increasing energy.
1. covalent bonds
2. hydrogen bonds
3. ionic bonds 4. dispersion forces (Van der Waals)
(A)
4, 2, 1, 3
(B)
2, 4, 1, 3
(C)
3, 2, 4, 1
(D)
2, 1, 3, 4
39. A compound with the molecular formula C6H14 reacted with chlorine in the presence of light to give 5
monochlorinated products. The compound is which of the following?
(A)
n-hexane
(B)
2,3-dimethylbutane
(C)
2-methylpentane
(D)
3-methylpentane
40. A hydrocarbon gave only one monochlorinated product when reacted with chlorine and heat. What is the
hydrocarbon?
(A)
neopentane
(B)
isobutane Either of these two would work
(C)
2,3-dimethylbutane
(D)
2,2,3,3-tetramethylbutane
41. In which of the following molecules is abstraction of a primary, a secondary and a tertiary hydrogen possible?
(A)
neopentane
(B)
isobutane
(C)
isopentane
(D)
cyclopentane
42. Light-catalyzed chlorination of a hydrocarbon is a good synthetic procedure for making which of the following
compounds?
1. 2-chlorobutane
2. neopentyl chloride
3. 2-chloro-2-methylpropane
(A)
2, 4
(B)
1, 2
(C)
3, 4
(D)
2, 3
4. cyclohexyl chloride
43. When 2-methylbutane and bromine react with light, what is the order of increasing amounts of products
having bromine in the indicated positions (least first)?
3
1
4
(A)
1, 2, 3, 4
(B)
2
4, 2, 3, 1
(C)
1, 4, 3, 2
(D)
2, 3, 4, 1
44. When isobutane and fluorine react, what is the ratio of the products, 1-fluoro-2-methylpropane to 2-fluoro-2methylpropane?
(A)
9:1
(B)
2:1
(C)
3:1
(D)
1:400
45. What is the most likely ratio of ethyl chloride to methyl chloride when one mole each of methane and ethane
are reacted with chlorine and heat?
(A)
1:1
(B)
6:4
(C)
400:1
(D)
4:6