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Organic Chemistry, 8e (Wade)
Chapter 7 Structure and Synthesis of Alkenes

1) Which of the following statements best describes the relative bond dissociation energies of the sigma
and pi bonds present in the carbon-carbon double bond of an alkene?
A) sigma > pi
B) pi > sigma
C) sigma = pi
D) cannot be estimated
Answer: A
Diff: 2
Section: 7.1

2) The carbon-carbon bond length in ethylene is ________ than the carbon-carbon bond length in
ethane, and the HCH bond angle in ethylene is ________ the HCH bond angle in ethane
A) shorter; smaller than
B) shorter; larger than
C) longer; smaller than
D) longer; larger than
E) longer; the same as
Answer: B
Diff: 1
Section: 7.2

3) Carbon-carbon single bonds tend to be ________ and ________ than carbon-carbon double bonds.
A) shorter, stronger
B) longer, stronger
C) shorter, weaker
D) longer, weaker
Answer: D
Diff: 1
Section: 7.2

4) Which of the following best approximates the CCC bond angle of propene?
A) 90°
B) 109°
C) 120°
D) 150°
E) 180°
Answer: C
Diff: 1
Section: 7.2

1
Copyright © 2013 Pearson Education, Inc.
5) Circle all atoms that are coplanar in the molecule below.

Answer:

Diff: 2
Section: 7.2

6) Draw the line energy orbital diagram for the outer shell of an sp2 hybridized carbon atom and explain
how a carbon/carbon double is formed.
Answer:

If we follow Hund's rule and fill each orbital with one electron and then promote one to the lone atomic
p orbital, there are single electrons in the three sp hybrid orbitals that can form sigma overlaps with 2-H
orbitals and one other sp2 hybridized carbon orbital. The atomic p orbital with one electron can then
form a pi bond by a side to side overlap with the other p orbital from the other sp2 hybridized carbon
atom.
Diff: 2
Section: 7.2

7) Why is rotation about the carbon-carbon double bond in alkenes prohibited while relatively free
rotation can occur about the carbon-carbon single bond in alkanes?
Answer: Rotation about the C C single bond in alkanes can occur without breaking the bond or
disrupting the orbital overlap. For rotation to occur about a C C, the π bond would have to be broken
since the p orbital overlap from which the bond is formed is disrupted by rotation.
Diff: 2
Section: 7.2

2
Copyright © 2013 Pearson Education, Inc.
8) What two atomic orbitals or hybrid atomic orbitals overlap to form the C H bond in ethylene?
A) C sp3 + H s
B) C sp2 + H s
C) C sp + H s
D) C p + H s
Answer: B
Diff: 3
Section: 7.2

9) What two atomic orbitals or hybrid atomic orbitals overlap to form the C C σ bond in ethylene?
A) C sp3 + C sp3
B) C sp3 + C sp2
C) C sp2 + C sp2
D) C sp3 + C p
E) C sp2 + C p
Answer: C
Diff: 3
Section: 7.2

10) What two atomic orbitals or hybrid atomic orbitals overlap to form the C C π bond in ethylene?
A) C sp3 + C sp3
B) C sp3 + C sp2
C) C sp2 + C sp2
D) C sp2 + C p
E) C p + C p
Answer: E
Diff: 3
Section: 7.2

11) Consider molecules with the formula C10H16. Which of the following structural features are not
possible within this set of molecules?
A) 2 triple bonds
B) 1 ring and 1 triple bond
C) 2 rings and 1 double bond
D) 2 double bonds and 1 ring
E) 3 double bonds
Answer: A
Diff: 1
Section: 7.3

3
Copyright © 2013 Pearson Education, Inc.
12) How many elements of unsaturation are implied by the molecular formula C6H12?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: B
Diff: 1
Section: 7.3

13) How many elements of unsaturation do molecules with a molecular formula of C6H6Cl6 have?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: B
Diff: 1
Section: 7.3

14) How many elements of unsaturation do molecules with a molecular formula of C8H4N2 have?
A) 2
B) 4
C) 6
D) 8
E) 10
Answer: D
Diff: 1
Section: 7.3

15) Which of the following molecular formulas corresponds to a monocyclic saturated compound?
A) C6H6
B) C3H7Br
C) C3H7N
D) C3H8O
Answer: C
Diff: 2
Section: 7.3

4
Copyright © 2013 Pearson Education, Inc.
16) How many elements of unsaturation are implied by the molecular formula C5H8O?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Diff: 2
Section: 7.3

17) How many elements of unsaturation are implied by the molecular formula C7H11Cl?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Diff: 2
Section: 7.3

18) A newly isolated natural product was found to have the molecular formula C15H28O2. By
hydrogenating a sample of the compound, it was determined to possess one p bond. How many rings
are present in the compound?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: B
Diff: 2
Section: 7.3

19) The prostaglandin precursor arachidonic acid has the molecular formula C20H32O2. Given that
arachidonic acid is an acyclic carboxylic acid that contains no carbon-carbon triple bonds, how many
carbon-carbon double bonds are present?
A) 2
B) 3
C) 4
D) 5
E) 6
Answer: C
Diff: 2
Section: 7.3

5
Copyright © 2013 Pearson Education, Inc.
20) The steroid testosterone has the molecular formula C19H28O2. Given that there are two P -bond in a
molecule of testosterone, how many rings are present in each molecule?
A) 2
B) 3
C) 4
D) 5
E) 6
Answer: C
Diff: 2
Section: 7.3

21) How many elements of unsaturation are implied by the molecular formula C5H5NO2?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: E
Diff: 3
Section: 7.3

22) How many elements of unsaturation are implied by the molecular formula C8H11N?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: E
Diff: 3
Section: 7.3

23) A chemist has isolated a new natural product and determined its molecular formula to be
C24H40O4. In hydrogenation experiments the chemist found that each mole of the natural product
reacted with two moles of H2. How many rings are present in the structure of the new natural product?
A) 2
B) 3
C) 4
D) 5
E) 6
Answer: B
Diff: 3
Section: 7.3

6
Copyright © 2013 Pearson Education, Inc.
24) Provide the proper IUPAC name for the alkene shown below.

CH2 CHCH2CH2CH2CH3
Answer: hex-1-ene
Diff: 1
Section: 7.4

25) Provide the proper IUPAC name for the alkene shown below.

Answer: cyclopentene
Diff: 1
Section: 7.4

26) Draw an acceptable structure for 4-ethylhept-1-ene.


Answer:

Diff: 1
Section: 7.4

27) Provide an acceptable name for (CH3)2CHCH=C(CH3)CH2CH3.


Answer: 2,4-dimethyl-3-hexene or 2,4-dimethylhex-3-ene
Diff: 2
Section: 7.4

28) Provide an acceptable name for (CH3CH2)2CHCH2CH=CH2.


Answer: 4-ethyl-1-hexene or 4-ethylhex-1-ene
Diff: 2
Section: 7.4

29) Which of the following alkenes can show geometric isomerism: 2,3-dichloro-2-pentene, 4-chloro-3-
ethyl-3-hexene, 3-chloro-2-methyl-2-butene, and 3-chloro-2-methyl-1-butene?
Answer: 2,3-dichloro-2-pentene
Diff: 2
Section: 7.4

7
Copyright © 2013 Pearson Education, Inc.
30) Name the compound shown below.

Answer: 2-propyl-1,3-cyclopentadiene or 2-propylcyclopenta-1,3-diene


Diff: 2
Section: 7.4

31) Provide the proper IUPAC name for the alkene shown below.

Answer: 6-bromo-1-methylcyclohexene
Diff: 2
Section: 7.4

32) Provide the proper IUPAC name for the alkene shown below.

Answer: (R)-3-ethyl-3-methylcyclohexene
Diff: 2
Section: 7.4

33) Draw an acceptable structure for 4-phenylbut-1-ene.


Answer:

Diff: 2
Section: 7.4

34) Draw an acceptable structure for 1,2-dimethylcyclohexene.


Answer:

Diff: 2
Section: 7.4

8
Copyright © 2013 Pearson Education, Inc.
35) Draw and name all alkenes which have the molecular formula C4H8.
Answer:

Diff: 2
Section: 7.4

36) Identify the correct name for the following structure.

A) 3-methoxy-5-methylcyclohepta-1,5-diene
B) 6-methoxy-1-methylcyclohepta-1,4-diene
C) 7-methoxy-5-methylcyclohepta-1,4-diene
D) 4-methoxy-2-methylcyclohepta-1,5-diene
Answer: B
Diff: 2
Section: 7.4

37) Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Answer: 2,5-dichloropent-1-ene
Diff: 2
Section: 7.4

38) Provide a correct IUPAC name for the structure below.

Answer: 5-bromo-2-methyl-1,3-cyclopentadiene
Diff: 3
Section: 7.4

9
Copyright © 2013 Pearson Education, Inc.
39) Draw and name the six alkenes which have the molecular formula C5H10.
Answer:

Diff: 3
Section: 7.4

40) For which of the following alkenes will cis- and trans- isomers not exist?

A) a) only
B) b) only
C) both a) and c)
D) d) only
E) both c) and d)
Answer: A
Diff: 1
Section: 7.5

41) Provide the proper IUPAC name for the alkene shown below.

Answer: (E)-3,5-dimethylhex-2-ene
Diff: 1
Section: 7.5

10
Copyright © 2013 Pearson Education, Inc.
42) Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?

A) E
B) Z
C) neither E nor Z
Answer: C
Diff: 2
Section: 7.5

43) Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?

A) E
B) Z
C) neither E nor Z
Answer: B
Diff: 2
Section: 7.5

44) Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?

A) E
B) Z
C) neither E nor Z
Answer: A
Diff: 2
Section: 7.5

11
Copyright © 2013 Pearson Education, Inc.
45) Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?

A) E
B) Z
C) neither E nor Z
Answer: A
Diff: 2
Section: 7.5

46) Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?

A) E
B) Z
C) neither E nor Z
Answer: C
Diff: 2
Section: 7.5

47) Provide a structure for (Z)-4-bromo-3-heptene.


Answer:

Diff: 2
Section: 7.5

48) Provide the structure of (Z)-1-chloro-1-fluoro-1-butene.


Answer:

Diff: 2
Section: 7.5

12
Copyright © 2013 Pearson Education, Inc.
49) Provide the proper IUPAC name for the alkene shown below.

Answer: (E)-3,4-dimethylhept-3-ene
Diff: 2
Section: 7.5

50) Provide the proper IUPAC name for the alkene shown below.

Answer: (Z)-5-chloropent-2-ene
Diff: 2
Section: 7.5

51) Provide the proper IUPAC name for the alkene shown below.

Answer: (E)-2-ethylhexa-1,4-diene
Diff: 2
Section: 7.5

52) Translate the following condensed structure to a line-angle structure.

(E) CH3CBrCH(CH2)2C(O)CH(CH3)2
Answer:

Diff: 2
Section: 7.5

13
Copyright © 2013 Pearson Education, Inc.
53) Name the alkene shown. Be sure to include the appropriate E or Z label necessary.

Answer: (E)-1-bromo-4-chlorohept-3-ene
Diff: 2
Section: 7.5

54) Draw an acceptable structure for (Z)-2-chloro-4-ethylhex-2-ene.


Answer:

Diff: 3
Section: 7.5

55) Provide the structure of the monomer from which PVC or poly(vinyl chloride) is made.
Answer: H2C CHCl
Diff: 1
Section: 7.6

56) Draw the structure of polyethylene.


Answer: -[CH2CH2]n-
Diff: 2
Section: 7.6

57) Draw the structure of poly(tetrafluoroethylene) or Teflon.


Answer: -[CF2CF2]n-
Diff: 2
Section: 7.6

58) The compound produced when 3-methylpent-2-ene undergoes hydrogenation in the presence of a
platinum catalyst is ________.
Answer: 3-methylpentane
Diff: 1
Section: 7.7

14
Copyright © 2013 Pearson Education, Inc.
59) Circle the alkene below which has the smallest heat of hydrogenation.

Answer:

Diff: 2
Section: 7.7

60) Which has the smaller heat of hydrogenation, (E)-2-pentene or (Z)-2-pentene? What is the structural
origin of this difference?
Answer: (E)-2-pentene has the smaller heat of hydrogenation. There is less steric strain between the
alkyl substituents in the (E)-isomer than in the (Z)-isomer.
Diff: 2
Section: 7.7

61) Using Zaitsev's rule, choose the most stable alkene among the following.
A) 1-methylcyclohexene
B) 3-methylcyclohexene
C) 4-methylcyclohexene
D) They are all of equal stability according to Zaitsev's rule.
Answer: A
Diff: 2
Section: 7.7

62) Using Zaitsev's rule, choose the most stable alkene among the following.
A) hex-1-ene
B) (E)-hex-2-ene
C) (Z)-hex-2-ene
D) They are all of equal stability according to Zaitsev's rule.
Answer: B
Diff: 2
Section: 7.7

15
Copyright © 2013 Pearson Education, Inc.
63) Using Zaitsev's rule, choose the most stable alkene among the following.
A) 1,2-dimethylcyclohexene
B) 1,6-dimethylcyclohexene
C) cis-3,4-dimethylcyclohexene
D) They are all of equal stability according to Zaitsev's rule.
Answer: A
Diff: 2
Section: 7.7

64) Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut-2-ene, and 3-methylbut-1-ene.


When each of these alkenes is subjected to catalytic hydrogenation (H2, Pt), a single product results.
Which of the following best describes the structural relationship among these products?
A) The products are cis-trans isomers.
B) The products are identical.
C) The products are constitutional isomers.
D) The products are enantiomers.
E) The products are diastereomers.
Answer: B
Diff: 2
Section: 7.7

65) Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most
heat upon hydrogenation)?
A) 2,3-dimethyl-2-butene
B) 2-methyl-2-butene
C) trans-2-butene
D) cis-2-butene
E) 1-hexene
Answer: E
Diff: 2
Section: 7.7

66) Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least
heat upon hydrogenation)?
A) 2,3-dimethyl-2-butene
B) 2-methyl-2-butene
C) trans-2-butene
D) cis-2-butene
E) 1-hexene
Answer: A
Diff: 2
Section: 7.7

16
Copyright © 2013 Pearson Education, Inc.
67) The trans isomers of cycloalkenes with rings containing fewer than ________ atoms are unstable at
room temperature.
Answer: 8
Diff: 2
Section: 7.7

68) Circle the most stable alkene in the set of isomers below.

Answer:

Diff: 2
Section: 7.7

69) Draw the alkene of formula C5H10 which evolves the most heat per mole upon hydrogenation.
Answer: CH2 CHCH2CH2CH3
Diff: 2
Section: 7.7

70) Does the alkene shown below violate Bredt's rule?

Answer: No
Diff: 2
Section: 7.7

71) Does the alkene shown below violate Bredt's rule?

Answer: No
Diff: 2
Section: 7.7

17
Copyright © 2013 Pearson Education, Inc.
72) Does the alkene shown below violate Bredt's rule?

Answer: Yes
Diff: 2
Section: 7.7

73) Does the alkene shown below violate Bredt's rule?

Answer: No
Diff: 2
Section: 7.7

74) Which sequence ranks the following compounds in order of increasing heat of hydrogenation,
ΔHhyd?

1 cis-2-butene 2 1-butene 3 cyclohexene

A) 3<1<2
B) 3<2<1
C) 2<1<3
D) 1<3<2
Answer: A
Diff: 2
Section: 7.7

18
Copyright © 2013 Pearson Education, Inc.
75) Circle the alkene isomer that has the largest heat of hydrogenation.

Answer:

Diff: 2
Section: 7.7

19
Copyright © 2013 Pearson Education, Inc.
76) Circle the most stable alkene in the set of isomers below.

Answer:

Diff: 2
Section: 7.7

77) Draw all likely alkene products in the following reaction and circle the product you expect to
predominate.

Answer: No alkene product likely.


Diff: 2
Section: 7.7

20
Copyright © 2013 Pearson Education, Inc.
78) There are three isomeric methylbutene structures. Draw each of them and then circle the isomer
with the highest heat of hydrogenation.
Answer:

Diff: 3
Section: 7.7

79) Which of the following cycloalkenes would be expected to be stable?

A) 1 & 2
B) 2 & 3
C) 2
D) 1 & 3
E) None are stable.
Answer: D
Diff: 3
Section: 7.7

80) Compare the relative heats of hydrogenation of cyclobutene and cyclopentene and explain the
difference in magnitude.
Answer: Cyclobutene's heat of hydrogenation is larger in magnitude than cyclopentene's by about 4
kcal/mol. This is due to additional ring strain introduced into the smaller ring by sp2 centers.
Diff: 3
Section: 7.7

21
Copyright © 2013 Pearson Education, Inc.
81) Which of the following compounds is an E isomer?

A)

B)

C)

D)

Answer: B
Diff: 3
Section: 7.7

82) Alkenes ________.


A) are relatively polar compounds
B) have lower boiling points than alcohols of similar molecular weight
C) are reasonably soluble in water
D) both A and B
E) none of the above
Answer: B
Diff: 2
Section: 7.8

83) Which has the higher boiling point, cis- or trans-hex-3-ene? Briefly explain your choice.
Answer: Cis-Hex-3-ene has the higher boiling point since it has a net molecular dipole moment while
the trans-isomer does not. The presence of a permanent molecular dipole allows for stronger
intermolecular attractions.
Diff: 2
Section: 7.8

84) Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong
base to give pent-2-ene as the only alkene product?
A) 1-chloropentane
B) 2-chloropentane
C) 3-chloropentane
D) 1-chloro-2-methylbutane
E) 1-chloro-3-methylbutane
Answer: C
Diff: 1
Section: 7.9

22
Copyright © 2013 Pearson Education, Inc.
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