Principles of General Organic and Biological Chemistry 2nd Edition Smith Test Bank

Principles of General Organic and
Biological Chemistry 2nd Edition Smith

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Chapter 11: Unsaturated Hydrocarbons
1. Which types of compounds are saturated hydrocarbons?

A) Alkenes
B) Aromatic hydrocarbons
C) Alkanes
D) Alkynes
E) All of the hydrocarbons above are unsaturated hydrocarbons.
Ans: C Difficulty: Easy
2. Which is the molecular formula of an alkyne?

A) C10H18 B) C9H18 C) C8H18 D) C10H20
Ans: A Difficulty: Easy
3. What is the IUPAC name of this compound?
A) cis-3-Pentene D) 1-Methyl-2-ethylpentene
B) cis-2-Pentene E) trans-3-Pentene
C) Ethylpropene
Ans: B Difficulty: Medium
A) 5-Ethyl-4-methyl-4-heptene D) 3-Ethyl-4-methyl-3-heptene
B) 3-Ethyl-4-methyl-3-hexene E) 3-Ethyl-4-propyl-2-pentene
C) 3-Ethyl-4-methyl-4-heptene
Ans: D Difficulty: Medium
Page 152
A) Methylbenzene D) 1-Methyl-1,2-cyclohexadiene
B) 2-Methyl-1,3-cyclohexadiene E) Toluene
C) 3-Methyl-1,3-cyclohexadiene
Ans: B Difficulty: Difficult
6. What is the structure of 2-methyl-3-hexene?

A)
B)
C) (CH3)2C=CHCH2CH2CH3
D) (CH3)2CHCH=CHCH2CH3
Page 153
7. What is the structure of 3-methylcycloheptene?

A)
B)
C)
D)
8. What is the IUPAC name for the compound CH3CH=CHCH2CH3?

A) Pentene B) 2,3-Pentene C) 3-Pentene D) 2-Pentene
Ans: D Difficulty: Easy
9. The compounds 1-pentene and cis-2-pentene are an example of a pair of

A) Isotopes. C) Constitutional isomers.
B) Stereoisomers. D) Identical molecules.
Ans: C Difficulty: Medium
10. The molecules cis-2-pentene and trans-2-pentene are an example of a pair of

A) Isotopes. C) Constitutional isomers.
B) Stereoisomers. D) Identical molecules.
Ans: B Difficulty: Easy
Page 154
11. Which structure is trans-3-hexene?

A)
B)
C)
D)
12. Which is NOT a valid IUPAC name of an alkene?

A) 2,3-Dimethyl-3-hexene C) 1-Ethylcyclopentene
B) 1-Butene D) 2-Butyl-3-methyl-2-nonene
Ans: D Difficulty: Difficult
13. Which name is a valid IUPAC name of an unsaturated hydrocarbon?

A) 2,3-Dimethyl-3-hexyne D) 5-Butylcyclohexene
B) trans-1-Hexene E) 2-Methyl-2-butene
C) trans-3-Pentyne
Ans: E Difficulty: Difficult
14. What configuration of a double bond is more common in naturally occurring fatty
acids?
A) cis B) trans C) cis and trans are equally likely to occur.
15. Which fatty acid has the highest melting point?

A) CH3(CH2)12COOH
B) CH3(CH2)2CH=CH(CH2)8COOH
C) CH3(CH2)2CH=CH(CH2)2CH=CH(CH2)4COOH
D) CH3(CH2)14COOH
Page 155
16. Which fatty acid has the lowest melting point?

A) CH3(CH2)12COOH
B) CH3(CH2)2CH=CH(CH2)8COOH
C) CH3(CH2)2CH=CH(CH2)2CH=CH(CH2)4COOH
D) CH3(CH2)14COOH
17. The compound levonorgestrel, shown below, contains several different functional
groups which allow it to be classified as more than one type of organic compound.
Which compound classification type for levonorgestrel is incorrect?
A) Alcohol B) Alkene C) Alkyne D) Ketone E) Aromatic

Ans: E Difficulty: Easy
18. What is the product of the reaction 2-pentene + H2 →

Pd
?
A) Pentane B) 2-Pentane C) Ethane + Propane D) 2-Pentyne
Ans: A Difficulty: Medium
Page 156
19. What product is formed from the reaction below?
A)
B)
C)
D)
20. What product is formed from the reaction below?
A)
B)
C)
D)
Page 157
21. What product is formed in the reaction below?
A)
B)
C)
D)
Page 158
22. What product is formed in the hydration reaction shown below?
A)
B)
C)
D)
23. Which synthetic polymer is not one of the six compounds, called the “Big Six,” that
account for 76% of the synthetic polymers produced in the U.S. each year?
A) Polyethylene terephthalate (PET) D) High-density polyethylene (HDPE)
B) Polystyrene (PS) E) Polypropylene (PP)
C) Polytetrafluoroethylene (Teflon)
Ans: C Difficulty: Easy
Page 159
24. What is the structure of ortho-dichlorobenzene?

A)
B)
C)
D)
25. What is the IUPAC name of the compound below?
A) 1,3-Dichloro-2-oxybenzene C) 2,6-Dichlorophenol
B) 1,3-Dichloro-2-hydroxylbenzene D) 1,5-Dichlorophenol
Page 160
26. What is the structure of anthracene?

A)
B)
C)
D)
Page 161
27. What product results when benzene undergoes the chlorination reaction below?
A)
B)
C)
D)
Page 162
28. What starting material in a hydrochlorination reaction would produce the compound
below?
A)
B)
C)
D)
29. What reagent (and catalyst, if necessary) is needed to convert 2-methyl-2-pentene to the
compound below?
A) H2SO4 B) H2O, H2SO4 C) CH3OH, H2SO4 D) H2O E) CH3OH

30. How many different products are formed in the hydration reaction of 2-pentene?
A) 1 B) 2 C) 3 D) None; 2-pentene does not undergo hydration.
31. How many different products are formed in the hydrogenation reaction of 2-pentene?
A) 1 B) 2 C) 3 D) None; 2-pentene does not undergo hydrogenation.
Page 163
32. What monomer is used to form the polymer below?
A)
B)
C)
D)
Ans: C Difficulty: Difficult
33. How many different products are formed in the reaction of p-dibromobenzene with Cl2,
using FeCl3 as a catalyst?
A) 1 B) 2 C) 3 D) 4
Ans: A Difficulty: Difficult
34. How many different products are formed in the reaction of m-dibromobenzene with Cl2,
using FeCl3 as a catalyst?
A) 1 B) 2 C) 3 D) 4
35. The compounds o-chlorophenol and m-chlorophenol are examples of

A) Molecules that are identical.
B) Molecules that are constitutional isomers.
C) Molecules that are stereoisomers.
D) Molecules that are isotopes.
Page 164
36. What is the product of the reaction below?
A)
B)
C)
D)
37. What is the IUPAC name of the compound below?
A) 5-Amino-1,3-dichloro-4-pentylbenzene
B) 3,5-Dichloro-2-pentylaniline
C) 1,3-Dichloro-5-nitro-4-pentylbenzene
D) 3,5-Dichloro-2-pentane aminobenzene
E) 2,4-Dichloro-1-pentylaniline
Page 165
38. Para-chlorotoluene is the name of an organic compound. Which of the following

statements concerning the structure of this compound is false?
A) The compound is an alkene.
B) The compound contains a ring of carbon atoms.
C) A chlorine atom and a methyl group are substituents present in this compound.
D) The substituents that are present have a 1,4 relationship.
39. Which statement concerning the compound 1-ethylcyclohexene is false?

A) It contains a ring of six carbons.
B) It contains one C=C bond.
C) It contains a two carbon substituent on the parent carbon chain.
D) It is a saturated hydrocarbon.
40. What is the IUPAC name for the compound below?
A) Benzene B) Hexane C) Toluene D) Cyclohexane

41. Which term correctly describes the relative position of the two substituents on the
benzene ring in the compound below?
A) trans B) syn C) para D) meta

Page 166
42. All commercially available sunscreens contain a benzene ring in the structure of the
active ingredient. Which of the following compounds might be effective as an active
ingredient in a commercial sunscreen?
A)
B)
C)
D)
E) All would be effective.

Page 167
43. What product results when 1-heptene undergoes the halogenation reaction shown?
A)
B)
C)
D)
44. Fats are solids at room temperature and are generally formed from fatty acids having a
large number of double bonds in their carbon chains.
A) True B) False
45. The double bonds in naturally occurring fatty acids are typically trans.
A) True B) False
46. Essential fatty acids cannot be synthesized by the human body and therefore must be
obtained in the diet.
A) True B) False
47. When 4,4-dimethyl-2-pentene adds H2 in the presence of a metal catalyst, the product is
4,4-dimethylpentane.
A) True B) False
48. When an alkene undergoes an addition reaction, new atoms replace the hydrogen atoms
on the carbons that are part of the double bond.
A) True B) False
Page 168
49. The addition of water to an alkene is called a hydrogenation reaction.

A) True B) False
50. When an oil is partially hydrogenated, all of the double bonds react with H2, giving a
product that has a higher melting point.
A) True B) False
51. Partial hydrogenation of soybean oil has the effect of decreasing the number of
carbon-carbon double bonds in the oil.
A) True B) False
52. Saturated oils are more susceptible than unsaturated fats to oxidation, giving them a
longer shelf life.
A) True B) False
53. Saturated and unsaturated fatty acids have a similar 3-D shape.
A) True B) False
54. An organic compound is classified as aromatic if it is cyclic and has a fragrant odor.
A) True B) False
55. The reaction below illustrates the polymerization of tetrafluoroethylene.
A) True B) False
56. Aromatic hydrocarbons and alkenes undergo the same kind of addition reactions.
A) True B) False
57. The common name for methylbenzene is aniline.

A) True B) False
Page 169
58. Compounds containing two or more benzene rings that share carbon–carbon bonds are
called polycyclic aromatic hydrocarbons (PAHs).
A) True B) False
59. Phenols are antioxidants.

A) True B) False
60. A common functional group in many antioxidants is a carbonyl group on a benzene

ring.
A) True B) False
61. The nitration of benzene is illustrated in the reaction below.
A) True B) False
62. Markovnikov's rule is used to predict the addition products of benzene.

A) True B) False
63. Aniline can be formed by the hydrogenation of nitrobenzene.

A) True B) False
64. When benzene undergoes a sulfonation reaction the product is the compound shown
below.
A) True B) False
65. Butter and lard are composed mostly of saturated fatty acids.
A) True B) False
Page 170
66. The IUPAC name of this compound is 5-butyl-5-methyl-3-heptyne.
A) True B) False
67. The IUPAC name of this compound is 3,4-dimethyl-2,4,6-octatriene.
A) True B) False
68. When benzo[a]pyrene is oxidized in the body, a potent carcinogen is formed.

A) True B) False
69. In the structure below, all of the carbon atoms have a trigonal planar shape.
A) True B) False
70. Naphthalene, shown below, is a planar molecule.
A) True B) False
71. The compound 2,3-dimethyl-2-butene has cis and trans stereoisomers.

A) True B) False
Page 171
72. Cis and trans isomers are constitutional isomers that differ in the location of a C=C
bond.
A) True B) False
73. There are three constitutional isomers of molecular formula C4H8 that contain a double
bond, and one of these isomers exhibits stereoisomerism.
A) True B) False
74. The C=C bond in the structure below has a syn configuration.
A) True B) False
75. An alkene has the general molecular formula CnH2n, where n is the number of carbons in
the compound.
A) True B) False
76. Alkynes have a general formula of CnH2n-2, where n is the number of carbons in the
compound.
A) True B) False
77. Each carbon atom in ethylene is tetrahedral.

A) True B) False
78. Unsaturated hydrocarbons are compounds that contain fewer than the maximum number
of hydrogen atoms per carbon atom.
A) True B) False
79. Fatty acids are carboxylic acids (RCOOH) with long carbon chains.
A) True B) False
80. Saturated fats are typically obtained from animal sources, while unsaturated oils are
common in vegetable sources.
A) True B) False
Page 172
81. The compounds cis-2-hexene and trans-3-hexene are related as stereoisomers.

A) True B) False
82. In 2-butene, when the two CH3 groups are on the opposite side of the double bond, the
compound is called the _____ isomer.
Ans: trans
Difficulty: Easy
83. As the number of double bonds in a fatty acid increases, the melting point of the fatty
acid _____.
Ans: Decreases
Difficulty: Medium
84. Hydrogenation is the addition of _____ to an alkene.

Ans: Hydrogen (H2)
Difficulty: Easy
85. When an alkene undergoes a halogenation reaction, the product is a/an _____.
Ans: Dihalide
Difficulty: Medium
86. Resonance structures are Lewis structures with the same arrangement of _____ but a
different arrangement of _____.
Ans: Atoms; Electrons
Difficulty: Medium
87. A student incorrectly names a compound as 4,6-diethyl-5-heptene. The correct IUPAC

name of this compound is _____.
Ans: 5-Ethyl-3-methyl-3-octene
Difficulty: Difficult
88. The IUPAC name of the compound below is _____.
Ans: 3-Methylcyclobutene
Difficulty: Medium
Page 173
89. The prefix used to designate the relative position of the two substituents in methyl
salicylate is _____.
Ans: ortho
Difficulty: Easy
90. Polymers are large molecules made up of repeating units of smaller molecules called
_____ that are covalently bonded together.
Ans: Monomers
Difficulty: Easy
91. Alkenes and alkynes have _____ (low/high) melting points and boiling points and are
_____ (soluble/insoluble) in water.
Ans: Low; Insoluble
Difficulty: Easy
Page 174

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Principles of General Organic and

Biological Chemistry 2nd Edition Smith

1. Which types of compounds are saturated hydrocarbons?

2. Which is the molecular formula of an alkyne?

3. What is the IUPAC name of this compound?

4. What is the IUPAC name of this compound?

5. What is the IUPAC name of this compound?

6. What is the structure of 2-methyl-3-hexene?

7. What is the structure of 3-methylcycloheptene?

Ans: B Difficulty: Medium

8. What is the IUPAC name for the compound CH3CH=CHCH2CH3?

9. The compounds 1-pentene and cis-2-pentene are an example of a pair of

10. The molecules cis-2-pentene and trans-2-pentene are an example of a pair of

11. Which structure is trans-3-hexene?

Ans: B Difficulty: Easy

12. Which is NOT a valid IUPAC name of an alkene?

13. Which name is a valid IUPAC name of an unsaturated hydrocarbon?

15. Which fatty acid has the highest melting point?

16. Which fatty acid has the lowest melting point?

A) Alcohol B) Alkene C) Alkyne D) Ketone E) Aromatic

18. What is the product of the reaction 2-pentene + H2 →

19. What product is formed from the reaction below?

Ans: B Difficulty: Medium

20. What product is formed from the reaction below?

Ans: B Difficulty: Medium

21. What product is formed in the reaction below?

Ans: B Difficulty: Difficult

22. What product is formed in the hydration reaction shown below?

Ans: B Difficulty: Difficult

24. What is the structure of ortho-dichlorobenzene?

Ans: A Difficulty: Medium

25. What is the IUPAC name of the compound below?

26. What is the structure of anthracene?

Ans: D Difficulty: Medium

Ans: D Difficulty: Medium

Ans: B Difficulty: Difficult

A) H2SO4 B) H2O, H2SO4 C) CH3OH, H2SO4 D) H2O E) CH3OH

32. What monomer is used to form the polymer below?

Ans: C Difficulty: Difficult

35. The compounds o-chlorophenol and m-chlorophenol are examples of

36. What is the product of the reaction below?

Ans: C Difficulty: Difficult

37. What is the IUPAC name of the compound below?

38. Para-chlorotoluene is the name of an organic compound. Which of the following

39. Which statement concerning the compound 1-ethylcyclohexene is false?

40. What is the IUPAC name for the compound below?

A) Benzene B) Hexane C) Toluene D) Cyclohexane

A) trans B) syn C) para D) meta

E) All would be effective.

Ans: C Difficulty: Medium

49. The addition of water to an alkene is called a hydrogenation reaction.

55. The reaction below illustrates the polymerization of tetrafluoroethylene.

57. The common name for methylbenzene is aniline.

59. Phenols are antioxidants.

60. A common functional group in many antioxidants is a carbonyl group on a benzene

61. The nitration of benzene is illustrated in the reaction below.

62. Markovnikov's rule is used to predict the addition products of benzene.

63. Aniline can be formed by the hydrogenation of nitrobenzene.

66. The IUPAC name of this compound is 5-butyl-5-methyl-3-heptyne.

67. The IUPAC name of this compound is 3,4-dimethyl-2,4,6-octatriene.

68. When benzo[a]pyrene is oxidized in the body, a potent carcinogen is formed.

70. Naphthalene, shown below, is a planar molecule.

71. The compound 2,3-dimethyl-2-butene has cis and trans stereoisomers.