Test Bank for General Organic and Biochemistry 8th Edition Katherine Denniston Download

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Chapter 11: The Unsaturated Hydrocarbons – Alkenes,
Alkynes, and Aromatics
1. Which of the following best describes the changes that occurred in the reaction shown
below?

A) An H atom and an –OH group have been added to the reactant.

B) An –OH group has been added to the reactant.
C) An –OH group has replaced an H atom on the ring.
D) Two H atoms have been added.
E) An –OH group has replaced a carbon atom on the ring.
Ans: A

2. An organic compound is classified as aromatic if it fits which of the following criteria?

A) It is fragrant.
B) It is cyclic.
C) It contains at least one C=C bond.
D) It contains a benzene ring.
E) It follows Markovnikov’s rule.
Ans: D

3. What is the IUPAC name of HCCH?

A) acetyne
B) butyne
C) ethyne
D) diyne
E) triyne
Ans: C

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

4. What is the product of the reaction shown below?

A)

B)

C)

D)

E)
Ans: B

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

A) heptyne
B) butyl methyl ethene
C) 1-methyl-2-butyl ethyne
D) 2-hexene
E) 2-heptyne
Ans: E

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

6. What is true about a compound with the name 3,3-dimethyl-1-butyne?

A) It is aromatic.
B) It contains a carbonyl group.
C) It contains a carbon-carbon double bond.
D) It contains a carbon-carbon triple bond.
E) It contains a benzene ring.
Ans: D

7. Which statement concerning the structure of the compound 1-ethylcyclohexene is

FALSE?
A) It contains a ring of six carbons.
B) It contains one C=C.
C) It contains a two-carbon alkyl substituent on the parent chain.
D) It is an alkene.
E) All of the above statements are true.
Ans: E

8. Which of the following compounds exists as cis-trans isomers?

A) 1-pentene
B) butane
C) 2-methyl-1-butene
D) 3-hexene
E) 2,3-dimethyl-2-butene
Ans: D

9. Which compound shown below is NOT an isomer of the molecular formula C5H8?

A)

B)
C)

D)

E)
Ans: C

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

10. What is the relationship between the two compounds shown below?

A) They are identical.

B) They are geometric isomers.
C) They are constitutional isomers.
D) They are conformational isomers.
E) They are not related.
Ans: B

11. In the food industry, what substance undergoes hydrogenation to produce margarine?
A) vegetable oils
B) cholesterol
C) wheat
D) eggs
E) lard
Ans: A

12. Bromine (Br2) is often used as a quick test for the presence of unsaturation in an
aliphatic hydrocarbon. Bromine in CCl4 is red. When bromine reacts with an alkene or
an alkyne, the alkyl halide formed is colorless; hence the disappearance of the red color
is a positive test for unsaturation. A student tested the contents of two vials, A and B,
both containing compounds with the molecular formula C6H12. Vial A decolorized
bromine, but vial B did not. How may the results for vial B be interpreted?
A) Vial B must contain a compound with only C−C single bonds.
B) Vial B must contain a compound with a triple bond.
C) Vial B must contain a compound with more than one C=C bond.
D) Vial B must contain a cyclic compound.
E) Vial B must contain a compound that is not a hydrocarbon.
Ans: D

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

13. What is the product of the following reaction?

A)

B)

C)

D)

E)

Ans: C

14. Which of the following correctly states Markovnikov’s rule as it applies to the addition
of the generic reagent HX to an alkene?
A) The hydrogen atom of the HX reagent adds to the carbon atom of the double bond
that has more alkyl groups attached to it.
B) The hydrogen atom of the HX reagent adds to the carbon atom of the double bond
that doesn’t have any hydrogen atoms attached to it.
C) The hydrogen atom of the HX reagent adds to the carbon atom of the double bond
that has more hydrogen atoms attached to it.
D) The X atom of the HX reagent adds to the carbon atom of the double bond which has
more halogen atoms attached to it.
E) The X atom of the HX reagent adds to the carbon of the double bond that is closer to
the end of the carbon chain.
Ans: C

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

15. Which structure correctly represents the major product of the following reaction?

A)

B)

C)

D)

E)
Ans: B

16. What is the name of the major product in the reaction shown below?

H
H 3C C CH3
C C
+ HCl
H2

CH3

A) 2-methyl-2-pentene
B) 2-chloro-2-methyl-2-pentene
C) 3-chloro-2-methylpentane
D) 2-methylpentane
E) 2-chloro-2-methylpentane
Ans: E

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

17. Polyvinyl chloride (PVC) is formed by addition polymerization of vinyl chloride,

CH2=CHCl. Which of the following depicts a representative section of the PVC
structure?

A)

B)

C)

D)

E)
Ans: B

18. Which of the following reactions is best suited to prepare the compound 2,2-
dibromopentane?
A)

B)

C)

D)

E)
Ans: B

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

19. What is the molecular formula of the structure shown below?

A) C6
B) C6H6
C) C6H10
D) C6H12
E) C6H14
Ans: B

20. Which term correctly describes the substitution pattern on the benzene ring in
Fenfluramine, one component of the appetite suppressant Fen-Phen?

A) trans
B) syn
C) meta
D) cis
E) ortho
Ans: C

21. What is the geometry and bond angle around a carbon atom which has one triple bond
and one single bond to its neighboring atoms?
A) linear, 180o D) trigonal, 180o
B) bent, 120o E) tetrahedral, 109.5o
o
C) trigonal planar, 120
Ans: A

22. Which of the following is the correct condensed formula for 2-butyne?
A) CHCCH2CH3 D) CH3CH2CH2CH3
B) CH3CCCH3 E) None of the choices are correct.
C) CH3CH=CHCH3
Ans: B

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

23. Sunscreens absorb UV radiation and protect the skin from its harmful effects.
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 of the compounds would be effective.
Ans: A

24. What is the IUPAC name of the following compound?

A) 1,1,2-trimethylethene D) 2-methyl-2-butene
B) 2-methylbuta-2-ene E) 2,3-dimethylbutene
C) 1,2-dimethylpropene
Ans: D

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

A) cis-2-butene D) trans-1,2-dimethylethene
B) trans-2-butene E) cis-1,2-dimethylbutene
C) cis-1,2-dimethylethene
Ans: A

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

26. What is the proper IUPAC name for an alkene that contains three carbon atoms?
A) 1-methylethene D) propane
B) 2-methylethene E) 1-propyne
C) propene
Ans: C

27. Provide the IUPAC name of the following compound:

A) cis-1,2-dibromopropane D) cis-1,2-dibromopropene
B) trans-1,2-dibromo-1-methylethene E) trans-1,2-dibromopropene
C) cis-1,2-dibromo-2-methylethene
Ans: D

28. What catalysts are often used in the hydrogenation of alkenes?

A) platinum, palladium, and nickel D) gold, silver, and aluminum
B) copper, chromium, and zinc E) platinum, gold, and silver
C) acid, base, and nickel
Ans: A

29. What is the structure and name of the product of the following reaction?

A) CH3CH2CHCH3, butane D) CH3CH2CH2CH3, propane

B) CH3CH2CH2CH3, butane E) None of the choices are correct.
C) CH3CH2CCH, butyne
Ans: B

30. What is the structure of the product of the following reaction?

A) CH3CH2O D) HOCH2CH2OH
B) CH3CH3 E) None of the choices are correct.
C) CH3CH2OH
Ans: C

31. What is the structure and name of the major product of the following reaction?
CH3CH=CH2 + HCl → ?
A) CH3CH2CH2Cl, 3-chloropropane D) CH3CH=CHCl, 1-chloro-1-propene
B) CH3CH2CH2Cl, 1-chloropropane E) There is no major product.
C) CH2CHClCH3, 2-chloropropane
Ans: C

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

32. What is the common name of the compound shown?

A) methylbenzene D) methylcyclohexene
B) toluene E) None of the choices are correct.
C) methyltoluene
Ans: B

33. The compound ortho-dichlorobenzene has substituents on which carbon atoms of the
benzene ring?
A) C1 and C2 D) C1 and C 5
B) C1 and C3 E) C1 only
C) C1 and C4
Ans: A

34. When 4,4-dimethyl-2-pentene adds H2 in an addition reaction, what is the name of the
product that results?
A) pentane
B) 2,2-dimethylpentane
C) 4,4-dimethylpentane
D) 4,4-dimethyl-2-pentane
E) 2,3-dihydro-4,4-dimethylpentane
Ans: B

35. Which of the following terms best describes the geometry around a carbon atom with
the bonding pattern shown?

A) tetrahedral B) straight C) saturated D) trigonal planar E) cyclic

Ans: D

36. Which of the following reactions would provide the highest yield of 3-bromohexane?
A)
B)
C)
D)
E) All would provide equal yields of 3-bromohexane.
Ans: B

37. What is the molecular formula of the simplest alkyne?

A) C2H4 B) CH4 C) C4H8 D) C2H2 E) C4H6
Ans: D

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

38. How many moles of hydrogen gas (H2) are needed to convert one mole of ethyne to
ethane?
A) 0.5 B) 1 C) 2 D) 3 E) 8
Ans: C

39. How many moles of hydrogen gas (H2) are needed to convert one mole of ethene to
ethane?
A) 1 B) 2 C) 3 D) 4 E) 8
Ans: A

40. What is the IUPAC name of the following compound?

A) 4-methyl-2-heptyne D) 4-propyl-2-pentyne
B) 4-methyl-5-heptyne E) 2-propyl-3-butyne
C) 4-ethyl-4-methylbutane
Ans: A

41. What is the IUPAC name of the following compound?

A) propene B) 1-methylethyne C) propyne D) acetylene E) 2-methylethyne

Ans: C

42. What is the IUPAC name of the following compound?

A) butene D) propene
B) cis-2-butene E) cis-1,2-butene
C) trans-2-butene
Ans: C

43. Which of the following is the correct molecular formula for cyclopentene?
A) C4H8 B) C5H8 C) C5H12 D) C5H10 E) C5H6
Ans: B

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

44. Acetylene (ethyne) is a gas at room temperature because its boiling point is -84°C.
What type of intermolecular forces hold molecules of acetylene together in a collection?

A) London dispersion forces

B) hydrogen bonding
C) ionic bonding
D) dipole-dipole forces
E) covalent bonds
Ans: A

45. Bombykol is a pheromone secreted by the female silkworm moth to attract males. This
compound contains two alkene double bonds. Which of the following correctly
describes the geometry around each?

A) The double bond at C10 is cis and the double bond at C12 is trans.
B) The double bonds at C10 and C12 are both cis.
C) The double bonds at C10 and C12 are both trans.
D) The double bond at C10 is trans and the double bond at C12 is cis.
E) It is impossible to tell from the line formula alone.
Ans: D

46. Which reaction type is most characteristic of alkenes?

A) substitution D) combination
B) addition E) decomposition
C) elimination
Ans: B

47. Which reaction may be used to convert an alkene to an alkane?

A) hydrohalogenation D) hydration
B) substitution E) hydrocarbonation
C) hydrogenation
Ans: C

48. Which of the following types of compounds is produced by the hydration of an alkene?
A) alkyne B) phenol C) alcohol D) aldehyde E) ketone
Ans: C

49. What type of product is formed in the reaction between an alkene and a hydrogen
halide?
A) alcohol B) alkyl halide C) triol D) aldehyde E) ketone
Ans: B

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

50. para-Chlorotoluene is the name of an organic compound. Based on its name, what
information about the structure of this compound is FALSE?
A) It is an alkene.
B) The structure contains a benzene ring.
C) A methyl group and a chlorine atom are present as substituents.
D) The substituents that are present have a 1,4 relationship.
E) All of the above information is true.
Ans: A

51. The polymer shown was formed by the addition polymerization of an alkene.

What is the molecular formula of the alkene which formed the polymer?
A) C2H2Cl2 B) C2H3Cl C) C3H5Cl D) C3H7Cl E) C4H6Cl2
Ans: B

52. What is the proper IUPAC name of the following compound?

A) toluene D) nitro-toluene
B) phenol E) 1,2-dimethylbenzene
C) para-dimethylbenzene
Ans: E

53. Which of the following reaction types is most characteristic of aromatic compounds?
A) substitution D) combination
B) addition E) decomposition
C) elimination
Ans: A

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

54. What product results when benzene undergoes the halogenation reaction below?

A)

B)

C)

D)
E) There is no reaction; benzene is unreactive toward bromine.
Ans: A

55. What are the bond angles around the carbon atoms in CH2=CH2?
A) 180o B) 150o C) 120o D) 109.5o E) 90o
Ans: C

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

A) trans-1-bromo-1-methyl-2-pentene D) cis-5-bromo-3-hexene
B) 2-bromohexene E) cis-1-bromomethyl-2-pentene
C) trans-2-bromo-3-hexene
Ans: C

57. What is the proper name of the product formed by the hydrogenation of 2-octene?
A) 2-octane B) 1-octene C) 2-octyne D) octane E) cyclooctane
Ans: D

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

58. What is the correct IUPAC name for the compound shown below?

A) 2-methyl-1-butene
B) 2-ethylpropene
C) cis-2-methyl-1-butene
D) trans-2-ethyl-2-methylbutene
E) trans-2-ethyl-2-methylethene
Ans: A

59. What are the health risks associated with trans-fatty acids?
A) elevates the levels of LDL (bad) cholesterol
B) lowers the level of HDL (good) cholesterol
C) increases the risk of developing type-2 diabetes
D) All of the choices are correct.
E) None of the choices are correct.
Ans: D

60. What is the IUPAC name of the simplest alkene?

A) cyclopropene B) methene C) propyne D) ethylene E) ethene
Ans: E

61. What is the name of the compound formed by the chlorination (addition of Cl2) of
propene?
A) 1,1-dichloropropane D) 1-chloropropane
B) 1,2-dichloropropane E) 2-chloropropane
C) 2,2-dichloropropane
Ans: B

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 Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

62. What is the major product formed by the hydration of propene?

A) D) OH
OH

B) OH E) O

C)

OH
Ans: C

63. Which of the following correctly match the IUPAC and common system for naming a
benzene with two groups attached?
A) 1,2-dichlorobenzene and meta-dichlorobenzene
B) 2-bromotoluene and ortho-bromotoluene
C) 1-bromo-2-chlorobenzene, para-bromochlorobenzene
D) 5-chlorotoluene, meta-chlorotoluene
E) Both B and C are correct.
Ans: B

64. What is the name of the organic product of the reaction of benzene and chlorine (with
FeCl3 as a catalyst)?
A) 2-chlrorobenzene D) 1-chlorobenzene
B) meta-dichlorobenzene E) chlorobenzene
C) 1,2-dichlorobenzene
Ans: E

65. Alkenes contain only double bonds.

Ans: False

66. The molecular formula of 3-octene is C8H16.

Ans: True

67. The common name of ethyne is acetylene.

Ans: True

68. Both 1-butene and 2-butene have cis- and trans-isomers.

Ans: False

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Test Bank for General Organic and Biochemistry 8th Edition Katherine Denniston Download

Chapter 11 The Unsaturated Hydrocarbons – Alkenes, Alkynes, and Aromatics

69. Margarine is made by the hydrogenation of vegetable oils.

Ans: True

70. Palladium is a catalyst used in hydrogenation.

Ans: True

71. Hydration of an alkene produces a ketone.

Ans: False

72. Polyvinyl chloride is a polymer that contains no double bonds.

Ans: True

73. The names ortho-dimethylbenzene and 1,2-dimethylbenzene represent the same

compound.
Ans: True

74. Aromatic compounds undergo addition reactions more readily than substitution
reactions because they are extremely stable compounds.
Ans: False

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