Chapter.11 Complete Test Bank Unsaturated Hydrocarbons

General, Organic, and Biochemistry, 10e (Denniston)

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.

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.

3) What is the IUPAC name of HC≡CH? 

A) acetyne

B) butyne

C) ethyne

D) diyne

E) triyne

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

A)

B)

C)

D)

E)

5) What is the IUPAC name of the compound shown below?

A) heptyne

B) butyl methyl ethene

C) 1-methyl-2-butyl ethyne

D) 2-hexene

E) 2-heptyne

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.

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 these are correct.

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

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

A)

B)

C)

D)

E)

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.

11) In the food industry, what substance undergoes hydrogenation to produce margarine?

A) vegetable oils

B) cholesterol

C) wheat

D) eggs

E) lard

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.

13) What is the product of the following reaction?

A)

B)

C)

D)

E)

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 that 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.

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

A)

B)

C)

D)

E)

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

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

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)

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

A)

B)

C)

D)

E)

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

A) C6

B) C6H6

C) C6H10

D) C6H12

E) C6H14

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

21) What is the geometry and bond angle around a carbon atom that has one triple bond and one single bond to its neighboring atoms?

A) linear, 180o

B) bent, 120o

C) trigonal planar, 120o

D) trigonal, 180o

E) tetrahedral, 109.5o

22) Which of the following is the correct condensed formula for 2-butyne?

A) CH≡CCH2CH3

B) CH3C≡CCH3

C) CH3CH=CHCH3

D) CH3CH2≡CH2CH3

E) None of the choices are correct.

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.

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

A) 1,1,2-trimethylethene

B) 2-methylbuta-2-ene

C) 1,2-dimethylpropene

D) 2-methyl-2-butene

E) 2,3-dimethylbutene

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

A) cis-2-butene

B) trans-2-butene

C) cis-1,2-dimethylethene

D) trans-1,2-dimethylethene

E) cis-1,2-dimethylbutene

26) What is the proper IUPAC name for an alkene that contains three carbon atoms?

A) 1-methylethene

B) 2-methylethene

C) propene

D) propane

E) 1-propyne

27) Provide the IUPAC name of the following compound:

A) cis-1,2-dibromopropane

B) trans-1,2-dibromo-1-methylethene

C) cis-1,2-dibromo-2-methylethene

D) cis-1,2-dibromopropene

E) trans-1,2-dibromopropene

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

A) platinum, palladium, and nickel

B) copper, chromium, and zinc

C) acid, base, and nickel

D) gold, silver, and aluminum

E) platinum, gold, and silver

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

A) CH3CH2CHCH3, butane

B) CH3CH2CH2CH3, butane

C) CH3CH2C≡CH, butyne

D) CH3CH2CH2CH3, propane

E) None of the choices are correct.

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

A) CH3CH2O

B) CH3CH3

C) CH3CH2OH

D) HOCH2CH2OH

E) None of the choices are correct.

31) What is the structure and name of the major product of the following reaction? CH3CH=CH2 + HCl → ?

A) CH3CH2CH2Cl, 3-chloropropane

B) CH3CH2CH2Cl, 1-chloropropane

C) CH2CHClCH3, 2-chloropropane

D) CH3CH=CHCl, 1-chloro-1-propene

E) There is no major product.

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

A) methylbenzene

B) toluene

C) methyltoluene

D) methylcyclohexene

E) None of the choices are correct.

33) The compound ortho-dichlorobenzene has substituents on which carbon atoms of the benzene ring?

A) C1 and C2

B) C1 and C3

C) C1 and C4

D) C1 and C 5

E) C1 only

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

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

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.

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

A) C2H4

B) CH4

C) C4H8

D) C2H2

E) C4H6

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

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

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

A) 4-methyl-2-heptyne

B) 4-methyl-5-heptyne

C) 4-ethyl-4-methylbutane

D) 4-propyl-2-pentyne

E) 2-propyl-3-butyne

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

A) propene

B) 1-methylethyne

C) propyne

D) acetylene

E) 2-methylethyne

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

A) 1,2-dimethylbutene

B) cis-2-butene

C) trans-2-butene

D) 1,2-dimethylethene

E) cis-1,2-dimethylbutene

43) Which of the following is the correct molecular formula for cyclopentene?

A) C4H8

B) C5H8

C) C5H12

D) C5H10

E) C5H6

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

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.

46) Which reaction type is most characteristic of alkenes?

A) substitution

B) addition

C) elimination

D) combination

E) decomposition

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

A) hydrohalogenation

B) substitution

C) hydrogenation

D) hydration

E) hydrocarbonation

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

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

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 these are correct.

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

What is the molecular formula of the alkene that formed the polymer?

A) C2H2Cl2

B) C2H3Cl

C) C3H5Cl

D) C3H7Cl

E) C4H6Cl2

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

A) toluene

B) phenol

C) para-dimethylbenzene

D) ortho-toluene

E) 1,2-dimethylbenzene

53) Which of the following reaction types is most characteristic of aromatic compounds?

A) substitution

B) addition

C) elimination

D) combination

E) decomposition

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.

55) What are the bond angles around the carbon atoms in CH2=CH2?

A) 180°

B) 150°

C) 120°

D) 109.5°

E) 90°

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

A) trans-1-bromo-1-methyl-2-pentene

B) 2-bromohexene

C) trans-2-bromo-3-hexene

D) cis-5-bromo-3-hexene

E) cis-1-bromomethyl-2-pentene

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

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

59) What are the health risks associated with trans-fatty acids?

A) elevated levels of LDL (bad) cholesterol

B) decreased levels of HDL (good) cholesterol

C) increased risk of developing type-2 diabetes

D) All of the choices are correct.

E) None of the choices are correct.

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

A) cyclopropene

B) methene

C) propyne

D) ethylene

E) ethene

61) What is the name of the compound formed by the chlorination (addition of Cl2) of propene?

A) 1,1-dichloropropane

B) 1,2-dichloropropane

C) 2,2-dichloropropane

D) 1-chloropropane

E) 2-chloropropane

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

A)

B)

C)

D)

E)

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) 2-bromotoluene and ortho-bromotoluene and 1-bromo-2-chlorobenzene, para-bromochlorobenzene

64) What is the name of the organic product in the reaction of benzene and chlorine (with FeCl3 as a catalyst)?

A) 2-chlrorobenzene

B) meta-dichlorobenzene

C) 1,2-dichlorobenzene

D) 1-chlorobenzene

E) chlorobenzene

65) Alkenes contain only double bonds.

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

67) The common name of ethyne is acetylene.

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

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

70) Palladium is a catalyst used in hydrogenation.

71) Hydration of an alkene produces a ketone.

72) Pyridine, shown below, is a heterocyclic aromatic compound.

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

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