Chapter Seventeen

Topic: Classification of Dienes

Section: 17.1
Difficulty Level: Easy
1. Which of the following compounds are isolated dienes?

II

IV

A)
B)
C)
D)
E)

I
II
III
IV
V

2. Which of the following compounds are conjugated dienes?

A)
B)
C)
D)
E)

I
II
III
IV
II & IV

II

III

III

IV

3. Which of the following compounds have conjugated double bonds?

IV

III

II

4. Which of the following compounds have isolated double bonds?

II

IV

III

5. Classify the following compounds as having cumulated, conjugated or isolated double

bonds?

II

III

IV

6. Which of the following compounds are cumulated dienes?

A)
B)
C)
D)
E)

4-methyl-1,3-heptadiene
5-methyl-2,6-heptadiene
2-methyl-2,4-heptadiene
4-methyl-1,4-heptadiene
5-methyl-2,3-heptadiene

7. Which of the following compounds are conjugated dienes?

A)
B)
C)
D)
E)

4-methyl-1,3-heptadiene
5-methyl-2,6-heptadiene
2-methyl-2,4-heptadiene
4-methyl-1,4-heptadiene
5-methyl-2,3-heptadiene

V
O

8. Which of the following compounds are isolated dienes?

A)
B)
C)
D)
E)

4-methyl-1,3-heptadiene
5-methyl-2,6-heptadiene
2-methyl-2,4-heptadiene
4-methyl-1,4-heptadiene
5-methyl-2,3-heptadiene

9. What is the IUPAC name for the following compound?

Cl

A)
B)
C)
D)
E)

1-chloro-1-methyl-2,5-cyclohexadiene
3-chloro-3-methyl-1,4-cyclohexadiene
6- chloro-6-methyl-1,4-cyclohexadiene
2- chloro-2-methyl-1,3-cyclohexadiene
None of these

10. What is the IUPAC name for the following compound?

A)
B)
C)
D)
E)

(2E, 4Z)-2,4-hexadiene
(2E, 4Z)-1,4-dimethyl-1,3-butadiene
(2Z, 4Z)-1,4-dimethyl-1,3-butadiene
(2Z, 4Z)-2,4-hexadiene
None of these

11. What is the IUPAC name for the following compound?

A)
B)
C)
D)
E)

(2E,4Z,6E)3,4,7,8tetramethyl-2,4,6heptatriene
(2Z,4E,)3,4,7trimethyl-2,4,6octatriene
(2E,4Z,6E)2,5,6,7tetramethyl-3,5,7heptatriene
(2E,4Z) 2,5,6trimethyl-3,5,7octatriene
(2E,4E,)2,5,6trimethyl-2,4,6octatriene

12. What is the IUPAC name for the following compound?

13. Provide the structure for (E)-1,3-pentadiene.

14. Provide the structure for (Z)-2-methyl-2,4-hexadiene.
15. Provide the structure for (1E,3Z)-1-methoxy-2-methyl-1,3-pentadiene.
H3CO

H3CO

OCH3

H3CO

H3CO

IV

A)
B)
C)
D)
E)

III

II

I
II
III
IV
V

16. Provide the structure for (3S,4E)-3-t-butyl-4-methyl-1,4-hexadiene.

17. Which one of the following dienes is most stable?
A)
B)
C)
D)
E)

CH3CH=CHCH=CHCH3
CH3CH=CHCH2CH=CH2
CH2=CHCH2CH2CH=CH2
CH2=CHCH(CH3)CH=CH2
CH3CH=C=CHCH2CH3

18. Which one of the following dienes is least stable?

A)
B)
C)
D)
E)

CH3CH=CHCH=CHCH3
CH3CH=CHCH2CH=CH2
CH2=CHCH2CH2CH=CH2
CH2=CHCH(CH3)CH=CH2
CH3CH=C=CHCH2CH3

19. Which one of the following dienes is least stable?

II

A)
B)
C)
D)

III

IV

I
II
III
IV

20. Which one of the following dienes is most stable?

II

A)
B)
C)
D)

III

IV

I
II
III
IV

21. Rank the following dienes in increasing order of stability (least to most).

A)
B)
C)
D)
E)

I<IV<III<II
III<II<I<IV
IV<II<III<I
II<IV<III<I
I<III<II<IV

II

III

IV

22. Which one of the following dienes will have the least heat of hydrogenation?

II

III

A)
B)
C)
D)
E)

IV

I
II
III
IV
V

23. Which one of the following dienes will have the highest heat of hydrogenation?

II
III

A)
B)
C)
D)
E)

IV

I
II
III
IV
V

24. Rank the following dienes in order of decreasing heat of hydrogenation (most to least).

II

III

IV

25. Rank the following dienes in order of decreasing heat of hydrogenation (most to least).

II

III

IV

26. Predict the product for the following reaction.

(CH3)3COK

Br

27. Predict the product for the following reaction.

Cl

(CH3)3COK

28. Provide the reagents necessary to carry out the following conversion.

Topic Provide the reagents necessary to carry out the following conversion.
OH
:
Prepa
rati9.
30. Provide the reagents necessary to carry out the following conversion.

31. Which one of the following represents the lowest energy -bonding molecular orbital of
1,3-butadiene?

A)
B)
C)
D)

I
II
III
IV

II

III

IV

32. Which one of the following represents the highest energy -antibonding molecular
orbital of 1,3-butadiene?

A)
B)
C)
D)

I
II
III
IV

II

III

IV

33. How many -bonding molecular orbitals does 1, 3-pentadiene have?

A)
B)
C)
D)
E)

1
2
3
4
none

34. How many electrons does the HOMO of 1, 3-pentadiene have in its excited state?
A)
B)
C)
D)
E)

1
2
3
4
none

35. How many electrons does the HOMO of 2, 4-hexadiene have in its ground state?
A)
B)
C)
D)
E)

1
2
3
4
0

36. How many electrons does the LUMO of 2, 4-hexadiene have in its ground state?
A)
B)
C)
D)
E)

1
2
3
4
0

37. Which one of the following represents the HOMO of 1,3, 5-hexatriene?

A)
B)
C)
D)
E)

I
II
III
IV
V

III

II

IV

38. Which one of the following represents the LUMO of 1,3, 5-hexatriene?

A)
B)
C)
D)
E)

III

II

IV

I
II
III
IV
V

Which major product(s) are formed for the following reaction?

HI
I

I
I

A)
B)
C)
D)
E)

II

III

IV

I
II
III
IV
V

40. Which one of the following compounds is not a product of reaction between 1,3butadiene and HBr?
A) (S)-3-bromo-1-butene
B) (R)-3-bromo-1-butene
C) (E)-1-bromo-2-butene
D) (Z)-1-bromo-2-butene
E) (Z)-2-bromo-2-butene
:

41. Predict the product(s) for the following reaction.

HCl

42. Predict the possible major products for the following reaction.

HBr

43. Predict the possible products for the following reaction and provide a curved arrow
mechanism for the formation of these products.
HBr

44. Provide the structure of the 1,4 addition product for the reaction of 1,3-hexadiene with
Br2/CCl4?
Br
Ans:
Br

45. Provide the structure of the 1,2 addition product for the following reaction.
Br2
CCl4

:
46.
A)
B)
C)
D)
E)

A thermodynamically-controlled reaction will yield :

the most stable product.
the product whose formation requires the smallest free energy of activation.
the product that can be formed in the fewest steps.
the product that is formed at the fastest rate.
None of these.

47.
A)
B)
C)
D)
E)

A reaction under kinetic control will yield :

the most stable product.
the product that can be formed in the fewest steps.
the product whose formation requires the smallest free energy of activation.
the product with the greatest potential energy.
None of these
:

48. Predict the major product for the following reaction.

HCl
00C

49. Predict the major product for the following reaction.

HCl
400C

50. Provide the structure for 1,2 addition product for the following reaction and explain why
it is a major product rather than 1,4 addition product.

HBr
400C

51. Predict the major product for the following reaction and explain why it is major product.
HBr
400C

52. Predict the major product for the following reaction.

HCl
00C

:
53. What is the correct classification of the following pericyclic reaction?
heat

A)
B)
C)
D)
E)

electrophilic addition
sigmatropic rearrangement
cycloaddition
electrocyclic reaction
C&D
:

54. What is the correct classification of the following pericyclic reaction?

A)
B)
C)
D)
E)

electrophilic addition
sigmatropic rearrangement
cycloaddition
electrocyclic reaction
C&D

55. What is the correct classification of the following pericyclic reaction?

+

A)
B)
C)
D)
E)

electrophilic addition
sigmatropic rearrangement
cycloaddition
electrocyclic reaction
C&D

56.
A)
B)
C)
D)
E)

Which statement is NOT true about the Diels-Alder reaction?

It is a [4+2] cycloaddition reaction.
The diene must be in the s-cis conformation to react.
Most Diels-Alder reactions are reversible.
It is a sigmatropic rearrangement.
Electron donating groups on the diene and electron withdrawing groups on the
dieneophile favor product formation.

57.
A)
B)
C)
D)
E)

The Diels Alder reaction is a concerted reaction, which means

The product contains a cyclic ring
The diene must be in the s-cis conformation to react.
All changes in bonding (bond making and bond breaking) occur simultaneously.
It is an endothermic reaction
Both exo and endo products are formed

58. Which of the following dienes can undergo the Diels-Alder reaction?

III

II

A)
B)
C)
D)
E)

IV

I
II
III
IV
All of the these

59. Which of the following diene(s) can not undergo the Diels-Alder reaction?

A)
B)
C)
D)
E)

I
II
III
IV
I & IV

IV

III

II

60. Which one of the following dienophiles is least reactive in the Diels-Alder reaction?
O

O
CN
OCH3

A)
B)
C)
D)
E)

I
II
III
IV
V

NO2

H3CO

OCH3

II

III

IV

61. Which one of the following dienophiles is most reactive in the Diels-Alder reaction?
O

OCH3
O

A)
B)
C)
D)
E)

I
II
III
IV
V

II

IV
III

62. Predict the product for the following Diels-Alder reaction.

O

A)
B)
C)
D)
E)
63.

II

CCH3

CCH3

IV

III

I
II
III
IV
none of these
Predict the product for the following Diels-Alder reaction.
O
COCH3

A)
B)
C)
D)
E)

I
II
III
IV
None of these

COCH3

CCH3

OCH3

OCH3

II

III

IV

64. Predict the product for the following Diels-Alder reaction.

N
C

+
C
C
N

65. Predict the major product for the following Diels-Alder reaction.
O
C
OH

OH
C
O

66. Predict the major product for the following Diels-Alder reaction.

67. Predict the major product for the following Diels-Alder reaction.
O
Cl

OCCH3

68. Predict the product for the following Diels-Alder reaction.

O

+
Excess
O

69. Predict the major product for the following Diels-Alder reaction.
O

70. Compound A is one of the intermediate products in the synthesis of the corticoid
hormone cortisone. Provide the structure of compound A.
O

Compound A

H3CH2CO
O

71. Predict the major product for the following Diels-Alder reaction.
H3CO

CH2OCH3

+
O2N

s:

72. Predict the major product for the following intramolecular Diels-Alder reaction and
provide a curved arrow mechanism for the formation of the product.
O

H3CO

OCH3

73. The following Diels-Alder reaction product is an intermediate in the synthesis of

Estrone. Provide the structure of the product.
O

+
H3CO
O

. The following Diels-Alder reaction product is an intermediate in the synthesis of

Cholesterol. Provide the structure of the product.
O
H3CO

+
CH3
O

75. What diene and dienophile would react to give the following Diels-Alder product?
O
COH

COH
O
O

COH

COH

+
COH

COH
O

II

O
O
COH
COH

+
COH
COH

III

O
O

A)
B)
C)
D)

I
II
III
IV

IV

76. What diene and dienophile would react to give the following Diels-Alder product?

A)
B)
C)
D)
E)

I
II
III
IV
V

+
III

II

IV

. What diene and dienophile would react to give the following Diels-Alder product?

CCH3
O

CCH3

CCH3

CCH3

I
O

II

O
CCH3

CCH3

A)
B)
C)
D)
E)

I
II
III
IV
V

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Medium

IV

III

78. What diene and dienophile would react to give the following Diels-Alder product?

CN

CN
CN

CN

CN

CN

III

II

CN

CN
CH2CH3

CN

+
IV

A)
B)
C)
D)
E)

NC

+
V

I
II
III
IV
V

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Easy
79. What diene and dienophile would react to give the following Diels-Alder product?

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Medium

80. What diene and dienophile would react to give the following Diels-Alder product?
O
O

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Medium
81. What diene and dienophile would react to give the following Diels-Alder product?
O

COCH3
O

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard
82. What diene and dienophile would react to give the following Diels-Alder product?
O

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard

83. What diene and dienophile would react to give the following Diels-Alder product?
O

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard
84. What diene and dienophile would react to give the following Diels-Alder product?

O2N

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard
85. The following product is formed by an intramolecular Diels-Alder reaction. Provide the
structure of the starting compound.

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard

86. What diene and dienophile would react to give the following Diels-Alder product?
O

Topic: Diels-Alder Reaction

Section: 17.7
Difficulty Level: Hard
87. What diene and dienophile would react to give the following Diels-Alder product?
O

CN

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Medium
88. Which of the following best describes the stereochemistry of ring closure and the
product for the following reaction?

A)
B)
C)
D)

disrotatory, cis-3,4-diethylcyclobutene
conrotatory, cis-3,4-diethylcyclobutene
disrotatory, trans-3,4-diethylcyclobutene
conrotatory, trans-3,4-diethylcyclobutene

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Medium

89. Which of the following best describes the stereochemistry of ring closure and the
product for the following reaction?
h

A)
B)
C)
D)

disrotatory, cis-3,4-diethylcyclobutene
conrotatory, cis-3,4-diethylcyclobutene
disrotatory, trans-3,4-diethylcyclobutene
conrotatory, trans -3,4-diethylcyclobutene

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Hard
90. Which of the following best describes the stereochemistry of ring closure and the
product for the following reaction?
h
(3E,5Z,7E)-3,5,7-decatriene
A)
B)
C)
D)

disrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
conrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
disrotatory, trans-5,6-diethyl-1,3-cyclohexadiene
conrotatory, trans -5,6-diethyl-1,3-cyclohexadiene

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Hard
91. Which of the following best describes the stereochemistry of ring closure and the
product for the following reaction?

(3E,5Z,7E)-3,5,7-decatriene
A)
B)
C)
D)

disrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
conrotatory, cis-5,6-diethyl-1,3-cyclohexadiene
disrotatory, trans-5,6-diethyl-1,3-cyclohexadiene
conrotatory, trans -5,6-diethyl-1,3-cyclohexadiene

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Medium

92. Predict the product for the following electrocyclic reaction.

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Medium
93. Predict the product for the following electrocyclic reaction.

Topic: Electrocyclic Reactions

Section: 17.9
Difficulty Level: Medium
94. Predict the product for the following electrocyclic reaction.

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium

95. Predict the product for the following Claisen rearrangement.

O

OH

OH

OH

II

A)
B)
C)
D)

OH

III

I
II
III
IV

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium
96. Predict the product for the following Cope rearrangement.

II

IV

A)
B)
C)
D)

I
II
III
IV

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium

III

IV

97. Predict the product for the following reaction.

OH

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium
98. Predict the product for the following Claisen rearrangement and provide the curved
arrow mechanism for formation of the product.
O

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium
99. Predict the product for the following Cope rearrangement and provide the curved arrow
mechanism for formation of the product.

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium

100. Predict the product for the following reaction and provide the curved arrow mechanism
for formation of the product.

Topic: Sigmatropic Rearrangement

Section: 17.10
Difficulty Level: Medium
101. Provide the structures of A, B and C for the following reaction sequence.
OH

1. NaOH
2.

A
Br

1. NaOH
C
2. CH3CH2Br

Topic: UV-Vis Spectroscopy

Section: 17.11
Difficulty Level: Easy
102.
A)
B)
C)
D)
E)

Absorption of UV-visible radiation by a molecule results in___________ transitions.

electronic
nuclear
rotational
vibrational
None of these

Topic: UV-Vis Spectroscopy

Section: 17.11
Difficulty Level: Easy

103.
A)
B)
C)
D)
E)

Which is the most energetically favorable UV transition for 1,3-butadiene?.

n
*
n
*
2
3*

*
1
4*

Topic: UV-Vis Spectroscopy

Section: 17.11
Difficulty Level: Medium
104. Which of the following compound(s) have the longest max?
A)
B)
C)
D)
E)

(E) 2-pentene
(Z) 2-pentene
pentene
hexadiene
hexatriene

Topic: UV-Vis Spectroscopy

Section: 17.11
Difficulty Level: Medium
105. Which of the following compound(s) have the longest max?

IV

A)
B)
C)
D)
E)

I
II
III
IV
V

III

II

Topic: UV-Vis Spectroscopy

Section: 17.11
Difficulty Level: Medium
106. Which of the following compound(s) have the longest max?

A)
B)
C)
D)
E)

I
II
III
IV
V

CH=CHCH=CH2

CH=CHCH=CH2

CH=CHCH=CH2

CH=CHCH=CH2

II

III

IV

CH=CHCH=CH2