Full Test Bank Conjugated Unsaturated Systems Chapter 13

Package Title: Solomons Test Bank

Course Title: Solomons 13e

Chapter Number: 13

Question type: Multiple choice

1) The allyl radical has how many bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

2) The allyl radical has how many electrons in bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

3) The allyl radical has how many electrons in non-bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

4) The allyl radical has how many  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

5) The HOMO of the allylic radical has how many electrons in its ground state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

6) The LUMO of the allylic radical has how many electrons in its ground state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

7) The HOMO of the allylic cation has how many electrons in its ground state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.2

Difficulty Level: Medium

8) The allyl cation has how many electrons in bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.3

Difficulty Level: Medium

9) The allyl cation has how many bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.3

Difficulty Level: Medium

10) The allyl cation has how many  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Molecular Orbitals

Section: 13.3

Difficulty Level: Medium

11) 1,3-Pentadiene has how many bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

12) 1,3-Butadiene has how many bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

13) 1,3-Pentadiene has how many antibonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.7

Difficulty Level: Medium

14) 1,3-Butadiene has how many electrons in its ground state bonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

15) 1,3-Butadiene has how many electrons in its ground state antibonding  molecular orbitals?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

16) The HOMO of 1,3-pentadiene has how many electrons in its ground state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

17) The LUMO of 1,3-pentadiene has how many electrons in its ground state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

18) The HOMO of 1,3-pentadiene has how many electrons in its excited state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

19) The LUMO of 1,3-pentadiene has how many electrons in its excited state?

a) 1

b) 2

c) 3

d) 4

e) 0

Topic: Molecular Orbitals

Section: 13.6

Difficulty Level: Medium

20) Which carbocation would be least stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

21) Which carbocation would be least stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

22) Which carbocation would be most stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

23) Which carbocation would be most stable?

a)

b)

c)

d)

e)

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

24) Which carbocation would be least stable?

a)

b)

c)

d)

e)

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

25) Which carbocation would be most stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

26) Which carbocation would be most stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

27) Which of the following dienes would you expect to be the most stable?

a) CH₃CH=CHCH=CHCH₃

b) CH₃CH=CHCH₂CH=CH₂

c) CH₂=CHCH₂CH₂CH=CH₂

d) CH₂=CHCH(CH₃)CH=CH₂

e) CH₃CH=C=CHCH₂CH₃

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.8

Difficulty Level: Easy

28) Which of the following dienes would you expect to be the most stable?

a) CH₃CH₂CH=CHCH₂CH=CHCH₃

b) CH₃CH=CHCH=CHCH₂CH₃

c) CH₂=CHCH₂CH₂CH₂CH=CH₂

d) CH₂=CHCH=CHCH₂CH₂CH₃

e) CH₃CH₂CH=C=CHCH₂CH₃

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Easy

29) Which of the following compounds would be the most stable?

a) I

b) II

c) III

d) IV

e) They are all of equal stability.

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Easy

30) Which diene would be least stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Easy

31) Which of the following dienes would you expect to be the most stable?

a) CH₃CH₂CH=CHCH₂CH=CHCH₃

b) CH₃CH=CHCH=CHCH₂CH₃

c) CH₂=CHCH₂CH₂CH₂CH=CH₂

d) CH₂=CHCH=CHCH₂CH₂CH₃

e) CH₃CH=C(CH₃)CH=CHCH₂CH₃

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

32) Which of the following dienes would you expect to be the least stable?

a) CH₃CH₂CH=CHCH₂CH=CHCH₃

b) CH₃CH=CHCH=CHCH₂CH₃

c) CH₂=CHCH₂CH₂CH₂CH=CH₂

d) CH₂=CHCH=CHCH₂CH₂CH₃

e) CH₃CH=C(CH₃)CH=CHCH₂CH₃

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

33) Considering both configurational and conformational factors, select the most stable form of 2,4-hexadiene.

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

34) Considering both configurational and conformational factors, select the least stable form of 2,4-hexadiene.

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

35) Which alkene would you expect to be most stable?

a) CH₂=CHCH₂CH₂CH=CH₂

b)

c)

d)

e)

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

36) Arrange these hexadienes in order of expected decreasing stability.

a) V > II > I > III > IV

b) III > IV > II > I > V

c) IV > III > II > V > I

d) IV > III > I > II > V

e) I > II > IV > III > V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

37) Arrange these hexadienes in order of expected increasing stability.

a) V < II < I < III < IV

b) III < IV < II < I < V

c) IV < III < II < V < I

d) IV < III < I < II < V

e) I < II < IV < III < V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.7

Difficulty Level: Medium

38) Arrange these carbocations in order of expected increasing stability.

a) V < II < I < IV < III

b) V < I < II < IV < III

c) IV < I < II < V < III

d) IV < III < I < II < V

e) I < II < IV < III < V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Medium

39) Arrange these carbocations in order of expected increasing stability.

a) V < II < I < IV < III

b) V < I < II < IV < III

c) IV <I < II < V < III

d) IV < III < I < II < V

e) II < III < IV < V < I

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Medium

40) Which is not an example of resonance?

a) I

b) II

c) III

d) IV

e) None of these choices are examples of resonance.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

41) Which is not an example of resonance?

a) I

b) II

c) III

d) IV

e) None of these choices are examples of resonance.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

42) Which is not a proper resonance structure for 1,3-butadiene?

a) CH₂=CH–CH=CH₂

b)

c)

d)

e) All of these answer choices are correct.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

43) Which pair does not represent a pair of resonance structures?

a) I

b) II

c) III

d) IV

e) All of these choices represent pairs of resonance structures.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

44) Which pair does not represent a pair of resonance structures?

a) I

b) II

c) III

d) IV

e) All of these choices represent pairs of resonance structures.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

45) Which pair does not represent a pair of resonance structures?

a) I

b) II

c) III

d) IV

e) All of these choices represent pairs of resonance structures.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

46) Which pair does not represent a pair of resonance structures?

a) I

b) II

c) III

d) IV

e) All of these choices represent pairs of resonance structures.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

47) Which pair does not represent a pair of resonance structures?

a) I

b) II

c) III

d) IV

e) All of these choices represent pairs of resonance structures.

Topic: Resonance

Section: 13.4

Difficulty Level: Easy

48) Select the structure of the conjugated diene.

a) I

b) II

c) III

d) IV

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

49) Select the structure of the conjugated diene.

a) I

b) II

c) III

d) IV

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

50) Select the structure of the conjugated diene.

a) I

b) II

c) III

d) IV

e) V

Topic: Alkene Classification

Section: 13.6

Difficulty Level: Easy

51) Select the structure of the isolated diene.

a) I

b) II

c) III

d) IV

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

52) Select the structure(s) of the conjugated diene(s).

a) I and II

b) II and III

c) III and IV

d) I, II and V

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

53) Which of the following dienes is a cumulated diene?

a) CH₂=CHCH₂CH₂CH=CH₂

b) CH₂=CHCH=CHCH₂CH₃

c) CH₃CH=C=CHCH₂CH₃

d) CH₃CH=CHCH=CHCH₃

e) CH₃CH=CHCH₂CH=CH₂

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

54) Which of the following dienes is a cumulated diene?

a) CH₂=CHCH₂CH₂CH₂CH=CH₂

b) CH₂=CHCH=CHCH₂CH₂CH₃

c) CH₃CH=C=CHCH₂CH₂CH₃

d) CH₃CH=CHCH=CHCH₂CH₃

e) CH₃CH₂CH=CHCH₂CH=CH₂

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Easy

55) Select the structure(s) in which the multiple bonds are conjugated.

a) I and II

b) II and III

c) III and IV

d) I, II and V

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Medium

56) Select the structure(s) in which the multiple bonds are conjugated.

a) I and IV

b) II and III

c) III and V

d) I, II and III

e) V

Topic: Alkene Classification

Section: 13.5

Difficulty Level: Medium

57) What is an IUPAC name for

a) 2,3-methylhept-2-en-4-yne

b) 1,1,3-trimethylhex-3-yn-1-ene

c) 1,1,3-trimethyl-3-hexyn-1-ene

d) 2,3-dimethyl-2-hepten-4-yne

e) 5,6-dimethyl-5-hepten-3-yne

Topic: Nomenclature

Section: 4.5, 4.6 and 13.5

Difficulty Level: Medium

58) A correct IUPAC name of the compound below is:

a) 1-Bromo-1-methyl-2,5-cyclohexadiene

b) 3-Bromo-3-methyl-1,4-cyclohexadiene

c) 6-Bromo-6-methyl-1,4-cyclohexadiene

d) 2-Bromo-2-methyl-1,3-cyclohexadiene

e) None of these choices.

Topic: Nomenclature

Section: 4.5, 4.6 and 13.5

Difficulty Level: Medium

59) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Medium

60) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.6

Difficulty Level: Medium

61) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Medium

62) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Medium

63) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Medium

64) The substituent R on the bicyclic compound shown is considered to be?

a) axial

b) equatorial

c) endo

d) exo

e) Trans

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Medium

65) What is an IUPAC name for this triene?

a) (2E,4Z,6E)-2,4,6-Nonatriene

b) (2Z,4E,6Z)-2,4,6-Nonatriene

c) (2E,4Z,6Z)-2,4,6-Nonatriene

d) (3Z,5Z,7E)-3,5,7-Nonatriene

e) (3Z,5E,7E)-3,5,7-Nonatriene

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Hard

66) What is an IUPAC name for this triene?

a) (2E,4Z,6E)-3,4,7,8-tetramethyl-2,4,6-Nonatriene

b) (2Z,4E,6E)-3,4,7,8-tetramethyl-2,4,6-Nonatriene

c) (2E,4Z,6E)-2,3,6,7-tetramethyl-3,5,7-Nonatriene

d) (2E,4Z,6E)-2,3,6,7-tetramethyl-3,5,7-Nonatriene

e) (2E,4E,6E)-3,4,7,8-tetramethyl-2,4,6-Nonatriene

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Hard

67) Which compound would have the shortest carbon-carbon single bond?

a) CH₃–CH₃

b) CH₂=CH–CH₃

c) HCC–CCH

d) CH₂=CH–CCH

e) CH₂=CH–CH=CH₂

Topic: Bond Lengths

Section: 13.6

Difficulty Level: Easy

68) Which compound would have the shortest carbon-carbon single bond?

a) CHC–CH=CH–CH₂–CH₃

b) CH₂=CH–CH=CH–CH₃

c) HCC–CH₂–CC–CH₃

d) CH₂=CH–CC–CH₂–CH₃

e) CH₃–CC–CC–CH₃

Topic: Bond Lengths

Section: 13.6

Difficulty Level: Easy

69) Which carbon-carbon bond in the following compound would you expect to be shortest?

a) I

b) II

c) III

d) IV

e) V

Topic: Bond Lengths

Section: 13.6

Difficulty Level: Easy

70) Which carbon-carbon bond in the following compound would you expect to be longest?

a) I

b) II

c) III

d) IV

e) V

Topic: Bond Lengths

Section: 13.6

Difficulty Level: Easy

71) Which alkene would you expect to have the highest heat of hydrogenation?

a)

b)

c)

d)

e)

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Easy

72) Which alkene would you expect to have the smallest heat of hydrogenation?

a) CH₂=CHCH₂CH₂CH=CH₂

b)

c)

d)

e)

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

73) Which alkene would you expect to have the smallest heat of hydrogenation?

a)

b)

c)

d)

e)

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

74) Which alkene would you expect to have the lowest heat of hydrogenation?

a) I

b) II

c) III

d) IV

e) V

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

75) Which alkene would you expect to have the highest heat of hydrogenation?

a) I

b) II

c) III

d) IV

e) V

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

76) Which alkene would you expect to have the lowest heat of hydrogenation?

a) I

b) II

c) III

d) IV

e) V

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

77) Which alkene would you expect to have the lowest heat of hydrogenation?

a) I

b) II

c) III

d) IV

e) V

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

a) 13 kJ mol^-1

b) 15 kJ mol^-1

c) 28 kJ mol^-1

d) 239 kJ mol^-1

e) 112 kJ mol^-1

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Hard

a) 13 kJ mol^-1

b) 15 kJ mol^-1

c) 28 kJ mol^-1

d) 239 kJ mol^-1

e) 112 kJ mol^-1

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Hard

a) 13 kJ mol^-1

b) 21 kJ mol^-1

c) 8 kJ mol^-1

d) 120 kJ mol^-1

e) 112 kJ mol^-1

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Hard

81) Which compound would have a UV absorption band at longest wavelength?

a) I

b) II

c) III

d) IV

e) V

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

82) Which compound would have a UV absorption band at longest wavelength?

a) I

b) II

c) III

d) IV

e) V

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

83) Which compound would have a UV absorption band at longest wavelength?

a) I

b) II

c) III

d) IV

e) V

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

84) Select the most energetically favorable UV transition for 1,3-butadiene.

a) n  *

b) n  *

c) ₂  ₃*

d)   *

e) ₁  ₄*

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

85) Which compound would have a UV absorption band at longest wavelength?

a) I

b) II

c) III

d) IV

e) V

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

86) Which of these symbols is used in connection with the intensity of absorption in the UV-visible region?

a) 

b) 

c) 

d) 

e) 

Topic: UV-Vis Spectroscopy

Section: 13.8

Difficulty Level: Easy

87) Ignoring stereochemistry, the 1:1 reaction of bromine with 1,3-cyclohexadiene at 25 C in the dark and in the absence of peroxide forms which of these?

a) I

b) II

c) III

d) IV

e) Both I and II

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Medium

88) Ignoring stereochemistry, the 1:1 reaction of chlorine with 1,3-cyclohexadiene at 25 C in the dark and in the absence of peroxide forms which of these?

a) I

b) II

c) III

d) IV

e) Both I and II

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Medium

89) Keeping in mind stereochemistry, how many products are formed by the reaction of one equivalent of HBr with 2-methyl-1,3-cyclohexadiene?

a) 2

b) 4

c) 6

d) 8

e) 10

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Medium

90) Which of the following dienes might react with bromine in CCl₄ to yield 2,5-dibromo-3-hexene?

a) CH₂=CHCH₂CH₂CH=CH₂

b) CH₂=CHCH=CHCH₂CH₃

c) CH₃CH=C=CHCH₂CH₃

d) CH₃CH=CHCH=CHCH₃

e) CH₃CH=CHCH₂CH=CH₂

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Medium

91) Indicate which products would be obtained from the chlorination of 1,5-hexadiene at high temperature (500 C), using a 1:1 mole ratio of the reactants.

a) I and II

b) II and III

c) III and IV

d) IV and V

e) V and I

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Medium

92) Which reagent would convert 1,3-pentadiene into 3-penten-2-ol?

a) KMnO₄/^–OH

b) OsO₄

c) H₂O₂, then H₃O⁺

d) Cl₂/H₂O

e) H₃O⁺

Topic: 1,2 Reactions of Conjugated Dienes

Section: 13.9

Difficulty Level: Medium

93) Which reagent would convert 1,3-octadiene into 3-octen-2-ol?

a) KMnO₄/^–OH

b) OsO₄

c) H₂O₂, then H₃O⁺

d) Cl₂/H₂O

e) H₃O⁺

Topic: 1,2 Reactions of Conjugated Dienes

Section: 13.9

Difficulty Level: Medium

94) Which is the only compound which can be completely ruled out as a product of the reaction of 1,3-butadiene with HCl?

a) (S)-3-chloro-1-butene

b) (R)-3-chloro-1-butene

c) (E)-1-chloro-2-butene

d) (Z)-1-chloro-2-butene

e) (Z)-2-chloro-2-butene

Topic: Conjugate Addition Reactions

Section: 13.9

Difficulty Level: Hard

95) How could the following synthesis be carried out?

a) (1) Br₂/CCl₄; (2) CH₃CH₂MgCl, ether; (3) CH₃ONa/CH₃OH

b) (1) HBr, 80 C; (2) (CH₃CH₂)₂CuLi, ether

c) (1) HBr, 80 C; (2) Mg, ether; (3) CH₃CH₂OH, then H₃O⁺

d) More than one of these choices.

e) All of these choices.

Topic: Multistep Synthesis

Section: 13.9

Difficulty Level: Hard

96) How could the following synthesis be carried out?

a) (1) Br₂/CCl₄; (2) CH₃MgCl, ether; (3) CH₃ONa/CH₃OH

b) (1) HBr (1 eq); (2) (CH₃)₂CuLi, ether

c) (1) HBr (1eq); (2) Li, ether; (3) CuI; (4) CH₃Br

d) More than one of these choices.

e) All of these choices.

Topic: Multistep Reaction Synthesis

Section: 13.9

Difficulty Level: Hard

97) A thermodynamically-controlled reaction will yield predominantly:

a) the more/most stable product.

b) the product whose formation requires the smallest free energy of activation.

c) the product that can be formed in the fewest steps.

d) the product that is formed at the fastest rate.

e) the product which possesses the greatest potential energy.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Easy

98) An equilibrium-controlled reaction will yield predominantly:

a) the more/most stable product.

b) the product whose formation requires the smallest free energy of activation.

c) the product that can be formed in the fewest steps.

d) the product that is formed at the fastest rate.

e) the product which possesses the greatest potential energy.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Easy

99) A reaction under kinetic (or rate) control will yield predominantly:

a) the most stable product.

b) the product that can be formed in the fewest steps.

c) the product whose formation requires the smallest free energy of activation.

d) the product with the greatest potential energy.

e) the product with the least potential energy.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Easy

100) The accompanying diagram, which describes the fate of the intermediate in a reversible reaction, implies that:

a) the less stable product forms more rapidly.

b) the more stable product forms more rapidly.

c) product B will predominate at equilibrium.

d) the intermediate has a short lifetime.

e) No conclusions can be drawn as to either reaction rate or product stability.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Medium

101) The accompanying diagram, which describes the fate of the intermediate in a reversible reaction, implies that:

a) the less stable product forms more rapidly.

b) the more stable product forms more rapidly.

c) product B will predominate at equilibrium.

d) the intermediate has a short lifetime.

e) No conclusions can be drawn as to either reaction rate or product stability.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Medium

102) The accompanying diagram implies that:

a) the formation of A from B would be favored at high temperature.

b) the more stable product forms more rapidly from the intermediate species.

c) the formation of B from the intermediate is the rate-limiting step in the transformation of A into B

d) the formation of B from A is not a concerted reaction.

e) All of these statements are true.

Topic: Reaction Mechanisms and Control

Section: 13.9

Difficulty Level: Medium

103) Which is an untrue statement concerning the Diels-Alder reaction?

a) The reaction is a syn addition.

b) The diene must be in the s-cis conformation to react.

c) Most Diels-Alder reactions are reversible.

d) Generally, the adduct formed most rapidly is the exo product.

e) Electron donating groups on the diene and electron withdrawing groups on the dieneophile favor adduct formation.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Easy

104) Which of these dienes can undergo the Diels-Alder reaction?

a)

b)

c)

d)

e) All of these choices can undergo the Diels-Alder reaction.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Easy

105) Which of these dienes can undergo the Diels-Alder reaction?

a)

b)

c)

d)

e)

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Easy

106) Which of the following can undergo the Diels Alder reaction?

a) I and II

b) II and III

c) III and IV

d) I, II and V

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Easy

107) From the standpoint of reactivity, which is the poorest choice of dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

108) What is the product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

109) Which would be the best synthesis of the following compound?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

110) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

111) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

112) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

113) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

114) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

115) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

116) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

117) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

118) Which reaction would produce the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

119) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

a) I

b) II

c) III

d) IV

e) More than one of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

120) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

121) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

122) Which of the following pairs of compounds could be used as the basis for a Diels-Alder synthesis of the compound shown below?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

123) does not undergo the Diels-Alder reaction because:

a) ring systems cannot function as the diene component.

b) it cannot adopt the s-cis conformation.

c) it lacks electron-withdrawing groups.

d) it lacks strong electron-releasing groups.

e) the two double bonds are farther apart than in a non-cyclic conjugated system.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

124) does not undergo the Diels-Alder reaction as a diene because:

a) a ring system with isolated alkenes cannot function as the diene component.

b) it cannot adopt the s-cis conformation.

c) it lacks electron-withdrawing groups.

d) it lacks strong electron-releasing groups.

e) the two double bonds are farther apart than in a non-cyclic conjugated system.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

125) does not undergo the Diels-Alder reaction as a diene because:

a) a bicyclic ring system cannot function as the diene component.

b) it cannot adopt the s-cis conformation.

c) it lacks electron-withdrawing groups.

d) it lacks strong electron-releasing groups.

e) the two double bonds are farther apart than in a non-cyclic conjugated system.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

126) does not undergo the Diels-Alder reaction as a diene because:

a) a bicyclic ring system cannot function as the diene component.

b) it cannot adopt the s-cis conformation.

c) it lacks electron-withdrawing groups.

d) it lacks strong electron-releasing groups.

e) the two double bonds are farther apart than in a non-cyclic conjugated system.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

127) does not undergo the Diels-Alder reaction as a diene because:

a) a bicyclic ring system cannot function as the diene component.

b) it cannot adopt the s-cis conformation.

c) it lacks electron-withdrawing groups.

d) it lacks strong electron-releasing groups.

e) the two double bonds are further apart than in a non-cyclic conjugated system.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

128) Which of these dienes is the most reactive in the Diels-Alder reaction?

a)

b)

c)

d)

e)

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

129) Which of the following dieneophiles is most reactive in a Diels-Alder reaction:

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

130) Which of the following dieneophiles is most reactive in a Diels-Alder reaction:

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

131) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

132) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

133) Which diene would be least reactive toward Diels-Alder addition of maleic anhydride?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

134) What would be the product of the following reaction?

a) I

b) II

c) III

d) IV

e) All of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

135) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

136) Which of the following would afford a synthesis of the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

137) What is the product of the following Diels-Alder cycloaddition reaction:

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

138) Which of the following would afford a synthesis of the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

139) Which of the following would afford a synthesis of the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

140) Which of the following would afford a synthesis of the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

141) Which diene would you expect to react most rapidly with maleic anhydride?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

142) Which of these conjugated dienes can undergo a Diels-Alder reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

143) Which of these conjugated dienes can undergo a Diels-Alder reaction?

a) I

b) II

c) III

d) IV

e) All of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

144) Which of these dienes can undergo a Diels-Alder reaction?

a) I and V

b) I, II and V

c) III

d) IV

e) III and IV

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

145) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

146) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

147) Which diene and dienophile would you choose to synthesize the following compound?

a) I and VI

b) II and V

c) III and IV

d) IV and V

e) I and III

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

148) Which diene and dienophile would you choose to synthesize the following compound?

a) I and VI

b) II and V

c) III and IV

d) IV and V

e) I and III

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

149) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

150) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

151) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

152) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

153) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

154) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

155) Which compounds could be used in a Diels-Alder synthesis of

a) I and III

b) I and IV

c) II and III

d) II and IV

e) I and II

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

156) Which is the major product of the following reaction?

a) I + enantiomer

b) II

c) III + enantiomer

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

157) Which is the major product of the following reaction?

a) I + enantiomer

b) II

c) III + enantiomer

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

158) Which is the major product of the following reaction?

a) I

b) II

c) III + enantiomer

d) IV + enantiomer

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

159) Which is the major product of the following reaction?

a) I

b) II

c) III + enantiomer

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

160) Which is the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

161) Which diene and dienophile would you choose to synthesize the following compound?

a) I

b) II

c) III

d) IV

e) None of these choices.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

162) Which of these dienes is the most reactive in the Diels-Alder reaction?

a) 1,3-Butadiene

b) 1,4-Pentadiene

c) 2,3,-Dimethyl-1,3-butadiene

d) 1,2-Butadiene

e) 1,4-Cyclohexadiene

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Hard

163) Which of these dienes can undergo the Diels-Alder reaction?

a) 1,3-Pentadiene

b) 1,4-Pentadiene

c) 1,2-Butadiene

d) 1,4-Cyclohexadiene

e) All of these choices can undergo the Diels-Alder reaction.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Hard

164) Which of these dienes can undergo the Diels-Alder reaction?

a) 1,2-Heptadiene

b) 1,3-Heptadiene

c) 1,4-Heptadiene

d) 1,5-Heptadiene

e) 1,6-Heptadiene

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Hard

165) How would you synthesize:

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Hard

Question type: fill-in-the-blank

166) Systems that have a p orbital on an atom adjacent to a double bond are called ___ systems.

Topic: General

Section: 13.1

Difficulty Level: Easy

167) The hydrogen atom on a saturated (sp³) carbon adjacent to a double bond is called an ___ hydrogen.

Topic: General

Section: 13.1

Difficulty Level: Easy

168) The hydrogen atom on a carbon that is part of a double bond is called a ___ hydrogen.

Topic: General

Section: 13.1

Difficulty Level: Easy

169) Allylic radicals are ___ stable than tertiary radicals.

Topic: General

Section: 13.1

Difficulty Level: Easy

170) Vinyl cations are ___ stable than tertiary cations.

Topic: General

Section: 13.3

Difficulty Level: Easy

171) There are three types of polyenes (molecules containing two or more double bonds). They are: ___.

Topic: General

Section: 13.5

Difficulty Level: Easy

172) Polyenes in which single and double bonds alternate along the carbon chain are called ___.

Topic: General

Section: 13.5

Difficulty Level: Easy

173) UV-vis spectroscopy can be used to indicate whether ___ is present.

Topic: General

Section: 13.8

Difficulty Level: Easy

174) When the product distribution for a particular reaction reflects the relative stabilities of the products, the reaction is said to be under ___ control.

Topic: General

Section: 13.9

Difficulty Level: Easy

175) When the product distribution for a particular reaction reflects the relative rate at which the products are formed, the reaction is said to be under ___ control.

Topic: General

Section: 13.9

Difficulty Level: Easy

176) A thermodynamically-controlled reaction will yield predominantly: ___.

Topic: General

Section: 13.9

Difficulty Level: Easy

177) The Diels-Alder reaction is a cycloaddition between a conjugated ___ and a ___.

Topic: General

Section: 13.10

Difficulty Level: Easy

178) Stereochemically speaking, the Diels-Alder reaction is ___ and occurs with ___ of the dienophile stereochemistry.

Topic: General

Section: 13.10

Difficulty Level: Easy

179) A reaction under kinetic (or rate) control will yield predominantly: ___.

Topic: General

Section: 13.9

Difficulty Level: Medium

180) Conjugated dienes routinely undergo 1,2 and 1,4 addition reactions with a variety of electrophilic reagents; this suggests that ___ are likely intermediates during these reactions.

Topic: General

Section: 13.9

Difficulty Level: Medium

Question type: Molecular drawing

181) Draw the structural formula for (R)-5-bromo-2,5-dimethyl-1,3-cyclopentadiene, clearly indicating stereochemical details.

Topic: Nomenclature

Section: 4.5, 4.6, 5.7, and 13.5

Difficulty Level: Hard

182) Draw the structural formula for (2E,4Z,6E)-3,4,7,8-tetramethyl-2,4,6-nonatriene, clearly indicating stereochemical details.

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Hard

183) Draw the structural formula for (2Z,4Z,6Z)-3,4,8-trimethyl-2,4,6-nonatriene, clearly indicating stereochemical details.

Topic: Nomenclature

Section: 4.5, 4.6, 7.2 and 13.5

Difficulty Level: Hard

184) Predict the product(s) of the following reaction:

Topic Conjugate Addition

Section: 13.9

Difficulty Level: Medium

Question type: fill-in-the-blank

185) During Diels-Alder reactions, when two stereoisomer products, exo and endo, are possible, the ___ product is typically obtained as the major product.

Topic: Diels-Alder Reactions

Section: 13.10

Difficulty Level: Easy

Question type: Essay

186) What reagents would be needed to synthesize the following substance via the Diels-Alder reaction? Give stereochemical details, as relevant.

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

187) Which diene and dienophile would you use to prepare the following molecule using a Diels-Alder cycloaddition reaction:

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

188) Which diene and dienophile would you use to prepare the following molecule using a Diels-Alder cycloaddition reaction:

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

189) The first step in the total synthesis of synthetic cholesterol involves production of the intermediate structure shown. Which combination of diene and dieneophile will result in its preparation?

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

190) The structure below is an intermediate along the way to the production of synthetic morphine. It is produced through a Diels-Alder cycloaddition reaction. Which combination of diene and dieneophile will result in its preparation?

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

191) What combination of diene and dieneophile can be used to prepare the following compound through a Diels-Alder cycloaddition reaction:

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

192) Predict the product of the following Diels-Alder cycloaddition reaction:

Topic Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

193) Steroids are naturally occurring polycyclic compounds classified as lipids. The Diels-Alder reaction has been widely used in their preparation. Shown below is a precursor molecule used in a total steroid synthesis. What combination of diene and dieneophile can be used to prepare this compound through the use of a Diels-Alder cycloaddition reaction.

Topic Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium

194) Draw arrows to indicate the electron flow for the following intramolecular Diels-Alder cycloaddition reaction:

Topic: Diels-Alder Mechanism

Section: 13.10

Difficulty Level: Hard

195) Which diene and dienophile would you use to prepare the following molecule using a Diels-Alder cycloaddition reaction:

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Hard

196) Complete the following sequence of reactions, giving structural details of all key intermediates.

Topic: Multistep Reactions

Section: 13.10

Difficulty Level: Hard

197) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

198) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

199) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

200) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

201) Show the steps and reagents necessary to prepare the following compound with a Diels-Alder reaction incorporated in the synthesis. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10 Difficulty Level: Hard

202) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

203) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10

Difficulty Level: Hard

204) Show the steps and reagents necessary to prepare the following compound from organic compounds having six carbons or less. Use retrosynthetic analysis as a tool to guide your synthesis.

Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10 Difficulty Level: Hard

205) Which carbocation would be most stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

206) Which carbocation would be most stable?

a)

b)

c)

d)

e)

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

207) Which carbocation would be least stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

208) Which carbocation would be least stable?

a) I

b) II

c) III

d) IV

e) V

Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3

Difficulty Level: Easy

209) Which compound would have the longest carbon-carbon single bond?

a) CH₃–CH₃

b) CH₂=CH–CH₃

c) HCC–CCH

d) CH₂=CH–CCH

e) CH₂=CH–CH=CH₂

Topic: Bond Lengths

Section: 13.6

Difficulty Level: Easy

210) Which alkene would you expect to have the largest heat of hydrogenation?

a) CH₂=CHCH₂CH₂CH=CH₂

b)

c)

d)

e)

Topic: Heat of Hydrogenation

Section: 13.7

Difficulty Level: Medium

211) Which diene would you expect to react least rapidly with maleic anhydride?

a) I

b) II

c) III

d) IV

e) V

Topic: Diels-Alder Reaction

Section: 13.10

Difficulty Level: Medium