Deck 11: The Unsaturated Hydrocarbons: Alkenes, alkynes, and Aromatics

Question 1

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.

Answer 1

They are geometric isomers.

Question 2

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.

Answer 2

An H atom and an -OH group have been added to the reactant.

Question 3

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)

Answer 3

Question 4

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

Question 5

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.

Question 6

What is the IUPAC name of HC≡CH?

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

Question 7

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.

Question 8

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.

Question 9

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.

Question 10

What is the IUPAC name of the compound shown below? $\mathrm { CH } _ { 3 } \mathrm { C } \equiv \mathrm { CCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$

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

Question 11

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

A)

B)

C)

D)

E)

Question 12

What is the molecular formula of the structure shown below?

A)C₆
B)C₆H₆
C)C₆H₁₀
D)C₆H₁₂
E)C₆H₁₄

Question 13

What is the product of the reaction shown below?

A)

B)

C)

D)

E)

Question 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.

Question 15

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

A)vegetable oils
B)cholesterol
C)wheat
D)eggs
E)lard

Question 16

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

A)
$+ 2 \mathrm { HBr } \longrightarrow$
B)
$+2 \mathrm{HBr} \longrightarrow$
C)
$+ \mathrm { Br } _ { 2 } \longrightarrow$
D)
$+ \mathrm { Br } _ { 2 } \longrightarrow$
E)
$+ \mathrm { Br } _ { 2 } \longrightarrow$

Question 17

What is the product of the following reaction?

A)

B)

C)

D)

E)

Question 18

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

Question 19

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

Question 20

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

A)

B)

C)

D)

E)

Question 21

What is the structure and name of the product of the following reaction? $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } = \mathrm { CH } _ { 2 } + \mathrm { H } _ { 2 } \stackrel { \text { Pd, heat } } { \longrightarrow } \text { ? }$

A)CH₃CH₂CHCH₃,butane
B)CH₃CH₂CH₂CH₃,butane
C)CH₃CH₂C?CH,butyne
D)CH₃CH₂CH₂CH₃,propane
E)None of the choices are correct.

Question 22

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.

Question 23

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

Question 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

Question 25

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

Question 26

What is the structure of the product of the following reaction? $\mathrm { H } _ { 2 } \mathrm { C } = \mathrm { CH } _ { 2 } + \mathrm { H } _ { 2 } \mathrm { O } \stackrel { \text { acid catalyst } } { \longrightarrow } \text { ? }$

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

Question 27

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

Question 28

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

Question 29

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.

Question 30

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

Question 31

Which of the following reactions would provide the highest yield of 3-bromohexane?

A)
$+\mathrm{HBr} \longrightarrow$
B)
$+\mathrm{HBr} \longrightarrow$
C)
$+\mathrm{Br}_{2} \longrightarrow$
D)
$+ \mathrm { HBr } \longrightarrow$
E)All would provide equal yields of 3-bromohexane.

Question 32

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

Question 33

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,180^o
B)bent,120^o
C)trigonal planar,120^o
D)trigonal,180^o
E)tetrahedral,109.5^o

Question 34

What is the molecular formula of the simplest alkyne?

A)C₂H₄
B)CH₄
C)C₄H₈
D)C₂H₂
E)C₄H₆

Question 35

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

Question 36

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.

Question 37

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

Question 38

What is the common name of the compound shown?

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

Question 39

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

Question 40

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

Question 41

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

A)C₄H₈
B)C₅H₈
C)C₅H₁₂
D)C₅H₁₀
E)C₅H₆

Question 42

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.

Question 43

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

Question 44

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

Question 45

What is the IUPAC name of the following compound? $\mathrm { H } _ { 3 } \mathrm { C } - \mathrm { C } \equiv \mathrm { C } - \mathrm { H }$

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

Question 46

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

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

Question 47

Which reaction type is most characteristic of alkenes?

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

Question 48

What product results when benzene undergoes the halogenation reaction below? $+ \mathrm { Br } _ { 2 } \stackrel { \mathrm { FeBr } _ { 3 } } { \longrightarrow }$

A)

B)

C)

D)

E)There is no reaction; benzene is unreactive toward bromine.

Question 49

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.

Question 50

What is the proper IUPAC name of the following compound?

A)toluene
B)phenol
C)para-dimethylbenzene
D)ortho-toluene
E)1,2-dimethylbenzene

Question 51

What is the IUPAC name of the simplest alkene?

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

Question 52

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

Question 53

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

Question 54

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

Question 55

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

A)180°
B)150°
C)120°
D)109.5°
E)90°

Question 56

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

Question 57

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.

Question 58

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

Question 59

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

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

Question 60

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

Question 61

Margarine is made by the hydrogenation of vegetable oils.

Question 62

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

Question 63

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

Question 64

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

Question 65

The molecular formula of 3-octene is C₈H₁₆.

Question 66

Hydration of an alkene produces a ketone.

Question 67

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

Question 68

Palladium is a catalyst used in hydrogenation.

Question 69

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

A)

B)

C)

D)

E)

Question 70

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

Question 71

Pyridine,shown below,is a heterocyclic aromatic compound.

Question 72

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

Question 73

Alkenes contain only double bonds.

Question 74

The common name of ethyne is acetylene.