Test bank for organic chemistry 1st edition by klein

Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 77.. Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium 79.. Ans: Topic: Drawing

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Difficulty Level: Easy

1 Which of the following is a substitution reaction?

Ans: C

Chapter 7

Topic: Introduction to Substitution

Section 1

Ans: D

Chapter 7

Section 1

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5 Draw an example of a substitution reaction

Ans: Numerous options!

Section 1

6 What is the nucleophile in the following reaction? Ans: B

Section 1

7 What is the electrophile in the following reaction? Ans: A

Section 1

8 What is the leaving group in the following reaction? carbon

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9 What are two features typical of a leaving group?

Ans: 1 A leaving group withdraws electron density from the adjacent carbon, and

2 A leaving group can stabilize negative charge

Section 1

Difficulty Level: Medium

10 For the following reaction, label the nucleophile, electrophile, and leaving group Ans:

Section 1

11 What is the nucleophile in the following reaction?

Ans: A

Section 1

12 What is the electrophile in the following reaction?

Ans: B

Section 1

13 What is the leaving group in the following reaction?

Sulfur

Carbon

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14 Which of the following is the correct IUPAC name of the following structure? Chlorocyclopentane

15 Which of the following is the correct IUPAC name of the following structure? 3-Fluorobutane

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16 Which of the following is the correct IUPAC name of the following structure? 2-Bromo-3-butylpentane

17 Which of the following is the correct structure for a compound with the IUPAC name of 2-bromo-3-methylbutane?

Ans: A

Topic: Alkyl Halides

Section 2

18 Which of the following is the correct structure for a compound with the IUPAC name of 1-iodo-3-ethylcyclohexane?

Ans: B

Section 2

19 Which of the following is the correct structure for a compound with the IUPAC name of (2R)-2-fluorobutane?

Ans: D

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Section 2

20 Which of the following compounds has a tertiary carbon?

Ans: B

Section 2

21 Provide an IUPAC name for the following compound

Ans: 1,1-Dibromocyclopropane

Section 2

22 Provide an IUPAC name for the following compound

Ans: 2-Chloro-5-fluorohexane

Section 2

23 On the following compound, label all of the primary, secondary, and tertiary carbons

Ans:

Section 2

24 Identify the labeled carbon as primary, secondary, or tertiary

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Ans: tertiary

Section 2

Ans: primary

Section 2

Ans: secondary

Topic: Possible Mechanisms

Section 3

27 Provide a definition of a concerted reaction

Ans: All bond breaking and making occurs at the same time

Section 3

28 Which of the following is a reasonable definition of a concerted reaction?

It is a reaction which takes place in a series of steps

It is a reaction which produces a loud noise

It is a reaction in which all bond-breaking and bond-forming occurs at the same time

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It is a substitution reaction

Ans: C

Section 3

Difficulty Level: Hard

29 Provide examples of the 4 patterns for steps in the mechanisms of substitution reactions

Ans: 1 Nucleophilic attack, 2 Loss of a leaving group, 3 Proton transfer, and

4 Rearrangement

Section 3

30 Which of the following is not a possible step in a substitution reaction?

Ans: D

Section 3

31 Provide an arrow pushing mechanism for the following reaction

Ans:

Section 3

32 Provide an arrow pushing mechanism and product for the following reaction Ans:

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Section 3

33 When drawing an arrow-pushing mechanism, the tail of the arrow starts where?

At the bond that is being formed

At the bond that is being broken

At the source of electrons that is being moved

At the location to which the electrons are being moved

Ans: C or B

Section 3

34 When drawing an arrow-pushing mechanism, the head of the arrow goes where?

At the bond that is being formed

At the bond that is being broken

At the source of electrons that is being moved

At the location to which the electrons are being moved

Ans: D

Section 3

35 Which of the following shows the correct arrow for loss of a bromide leaving group?

Ans: A

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Section 3

36 Provide an arrow-pushing mechanism for the following (intramolecular) reaction

Ans:

Topic: SN2 Mechanism

Section 4

37 Which of the following is the rate law for the following SN2 reaction? Rate = k[1-bromopropane]

38 Write the rate law for the following SN2 reaction

Ans:

Section 4

39 Which of the following is the product of the following SN2 reaction?

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Ans: C

Section 4

40 Which of the following is the product of the following SN2 reaction? Ans: C

Section 4

41 Provide the SN2 product of the following reaction

Ans:

Section 4

42 Provide a mechanism for this reaction

Ans:

Section 4

43 Which of the following is a mechanism for an SN2 reaction?

Ans: C

Show arrows more carefully in B, C, D

Section 4

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44 Which of the following is the product of the following reaction? Ans: A

Section 4

45 Which of the following is the product of the following reaction? Ans: D

Section 4

46 Which of the following is the product of the following reaction? Ans: A

Section 4

47 What is the product of the following reaction?

Ans:

Section 4

48 What is the product of the following reaction?

Ans:

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Section 4

49 From the given starting material, how could you stereospecifically form the given product?

Ans:

Section 4

50 Rank the following substrates from most to least reactive in an SN2 reaction A>B>C>D

51 Rank the following substrates from most to least reactive in an SN2 reaction

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Section 4

54 Draw a reaction diagram for the following reaction

Ans:

Section 4

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55 Which of the following is the reaction diagram for an exothermic, concerted reaction?

Ans: C

Section 4

56 Given the following rate law, what will happen to the rate if the concentration of MeI is doubled?

Rate = k[Me3N][MeI]

It will be doubled

It will not change

It will decrease in half

It will increase very slightly

Ans: A

Section 4

57 Given the following rate law, what will happen to the rate if the concentration of both reactants is doubled?

Rate = k[Me3N][MeI]

A It will be doubled

B It will not change

C It will decrease in half

D It will increase 4-fold

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Ans: D

Section 4

58 Given the following rate law, what will happen to the rate if the concentration of MeI is doubled and the concentration of Me3N is halved?

Rate = k[Me3N][MeI]

A It will be doubled

B It will not change

C It will decrease in half

D It will increase very slightly

Ans: B

Section 5

59 Which of the following is the rate law for the following reaction?

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60 Provide the rate law for the following reaction

Ans:

Section 5

61 Draw a reaction diagram for the following SN1 reaction

Ans:

Section 5

62 Which of the following is a reaction diagram for an SN1 reaction that is endothermic?

Ans: B

Section 5

63 Rank the following substrates from most to least reactive in an SN1 reaction A>B>C>D

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A A>B>C>D

B A>B>D>C

C C>B>A>D

D D>A>B>C

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Ans: C

Section 5

67 Why is a tertiary alkyl halide more reactive in an SN1 reaction than a secondary alkyl halide?

Ans: The tertiary cation is more stable

Section 5

68 Provide a mechanism for the following SN1 reaction

Ans:

Section 5

69 Which of the following is the product of the following reaction?

Ans: D

Section 5

Ans: B

Section 5

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Ans: C

Section 5

Ans: A

Section 5

73 Provide the product of the following reaction

Ans:

Section 5

74 What is the product of the following reaction Include stereochemistry Ans:

Section 5

75 What is the product of the following reaction Include stereochemistry Ans: A

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Section 5

76 Why does a racemate form at the leaving group carbon in an SN1 reaction? Ans: Because the cationic intermediate is planar and there is equal likelihood of attack of the nucleophile from either face, leading to equal formation of both enantiomers

Topic: Drawing the Complete SN1 Mechanism

Section 6

77 Which of the following is a good leaving group?

78 What is the best leaving group in the following compound?

Ans:

Section 6

79 Circle the best leaving group in the following compound

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Ans:

Section 6

80 Which of the following must be protonated in order to be a good leaving group?

81 Which of the following nucleophiles will require a proton transfer step at the end of the reaction?

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82 Provide an example of a nucleophile that will require a proton transfer step at the end of the reaction

Ans: Any protic nucleophile (so there are many answers)

Section 6

83 Which of the following alkyl halides would likely undergo rearrangement during

an SN1 reaction?

Ans: B

Section 6

84 Which of the following is the major product for the following SN1 reaction? Ans: B

Section 6

85 Draw the anticipated major product for the following reaction

Ans:

Section 6

86 Draw an energy diagram for the following reaction

Ans:

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Section 6

87 Draw a mechanism for the following reaction

Ans:

Section 6

88 What is the anticipated major product for the following reaction? Ans:

Section 6

89 What is the mechanism for the following reaction?

Ans:

Section 6

90 What is the rate law for the following SN1 reaction?

Ans:

Section 7

91 For the following reaction, which of the following is the mechanism?

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92 For the following reaction, which of the following is the product? Ans: D

Section 7

93 For the following reaction, which of the following is the rate law? k[HBr]

94 Draw an energy diagram for the following reaction

Ans:

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Section 7

95 For the following reaction, which of the following is the mechanism?

96 For the following reaction, which of the following is the product? Ans: B

Section 7

97 For the following reaction, which of the following is the rate law? Rate = k[MeI]

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Section 7

98 Draw an energy diagram for the following reaction Ans:

Section 7

99 For the following reaction, provide the mechanism Ans:

Section 7

100 For the following reaction, draw the product

Ans:

Section 7

101 For the following reaction, provide the rate law

Ans:

Section 7

102 For the following reaction, provide an energy diagram Ans:

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