test bank for organic chemistry 1st edition by klein · topic: introduction to substitution section...

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Chapter 7

Topic: Introduction to Substitution

Section 1

Difficulty Level: Easy

1. Which of the following is a substitution

reaction? Ans: C Chapter 7 Topic: Introduction to

Substitution Section 1 Difficulty Level: Easy 2. Which of the following is a substitution

reaction? Ans: D Chapter 7 Topic: Introduction to

Substitution Section 1 Difficulty Level: Easy 3. Which of the following is a substitution

reaction? Ans: B

Topic: Introduction to

Substitution Section 1 Difficulty Level: Medium

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5. Draw an example of a substitution reaction.

Ans: Numerous options!

Topic: Introduction to Substitution

Section 1


6. What is the nucleophile in the following reaction?

Ans: B Topic: Introduction to

Substitution Section 1 Difficulty Level: Easy 7. What is the electrophile in the following

reaction? Ans: A


Substitution Section 1 Difficulty Level: Easy 8. What is the leaving group in the following

reaction? carbon bromide hydrogen

nitrogen

Ans: B


Substitution Section 1 Difficulty Level: Hard 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. Topic: Introduction to Substitution

Section 1 Difficulty Level: Medium 10. For the following reaction, label the nucleophile, electrophile, and

leaving group. Ans:


Substitution Section 1 Difficulty Level: Easy 11. What is the nucleophile in the following reaction?

12. What is the electrophile in the

following reaction? Ans: B


Substitution Section 1 Difficulty Level: Easy 13. What is the leaving group in the following

reaction? Sulfur

Carbon

Hydrogen

Iodide

Ans: D

Topic: Alkyl Halides

Section 2


14. Which of the following is the correct IUPAC name of the following

structure? Chlorocyclopentane 2-Chloro-1-methylcyclopentane 1-Methyl-2-chlorocyclopentane 1-Chloro-2-methylcyclopentane

Ans: D


Section 2 Difficulty

Level: Easy


structure? 3-Fluorobutane 2-Fluorobutane (S)-2-Fluorobutane (R)-2-Fluorobutane

Ans: C

Topic: Alkyl

Halides Section 2 Difficulty Level: Medium


structure? 2-Bromo-3-butylpentane (2S)-Bromo-4,5-

dimethylheptane 3,4-Dimethyl-6-bromoheptane

2-Bromo-4-methylhexane

Ans: B



Level: Easy

17. Which of the following is the correct structure for a compound with

the IUPAC name of 2-bromo-3-methylbutane?

Ans: A


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

Difficulty Level: Medium

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

Ans: D


Section 2


20. Which of the following compounds has a tertiary

carbon? Ans: B



Level: Easy

21. Provide an IUPAC name for the

following compound. Ans: 1,1-

Dibromocyclopropane Topic: Alkyl Halides Section 2 Difficulty Level: Medium 22. Provide an IUPAC name for the

following compound. Ans: 2-Chloro-5-

fluorohexane Topic: Alkyl Halides Section 2 Difficulty Level: Medium 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.

Ans: tertiary


Section 2


25. Identify the labeled carbon as primary, secondary,

or tertiary. Ans: primary Topic: Alkyl Halides


Level: Easy

26. Identify the labeled carbon as primary, secondary,

or tertiary. Ans: secondary

Topic: Possible

Mechanisms Section 3 Difficulty Level: Medium 27. Provide a definition of a concerted reaction.

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

Topic: Possible Mechanisms

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.

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

Topic: Possible

Mechanisms Section 3 Difficulty Level: Medium 31. Provide an arrow pushing mechanism for the following reaction.

32. Provide an arrow pushing mechanism and product for the following

reaction. Ans:


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

Topic: Possible

Mechanisms Section 3 Difficulty Level: Easy 34. When drawing an arrow-pushing mechanism, the head of the

arrow goes where?

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

Ans: A


Section 3


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

37. Which of the following is the rate law for the following SN2 reaction?

Rate = k[1-bromopropane] Rate = k[NaCN] Rate = k[NaCN][1-bromopropane]

Rate = k[NaCN]2

38. Write the rate law for the following SN2 reaction.

Ans:

Topic: SN2 Mechanism


Level: Easy

39. Which of the following is the product of the following SN2

reaction? Ans: C



Level: Hard

40. Which of the following is the product of the following SN2

reaction? Ans: C


Section 4 Difficulty Level: Medium 41. Provide the SN2 product of the following reaction.

42. Provide a mechanism for this reaction.

Ans:



Level: Easy

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

Ans: C Show arrows more carefully in B, C, D


Section 4


44. Which of the following is the product of the

following reaction? Ans: A



Level: Easy


following reaction? Ans: D



Level: Easy




Section 4 Difficulty Level: Medium 47. What is the product of the following reaction?

Ans:


Section 4


48. What is the product of the following

reaction? Ans:



Level: Hard

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

the given product?

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

A>B>C>D D>C>B>A A>C>B>D D>C>B>A

Ans: C



Level: Easy


A. A>B>C>D

B. D>C>B>A

C. C>B>A>D

D. D>C>B>A

Ans: C


Section 4


52. Rank the following substrates from most to least reactive in an SN2

reaction. A. A>B>C>D B. D>C>B>A C. C>B>A>D D. D>C>A>B


reaction. A. A>B>C>D B. C>D>B>A C. C>B>A>D D. D>C>B>A

Ans: B


Section 4


54. Draw a reaction diagram for the following

reaction. Ans:


Section 4 Difficulty Level: Medium 55. Which of the following is the reaction diagram for an exothermic,

concerted reaction?

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.

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.

Ans: D



Level: Easy

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?

A. It will be doubled. B. It will not change. C. It will decrease in half. D. It will increase very

slightly. Ans: B

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

Rate = k[H2O]

Rate = k[H2O][1-chloro-1-methylcyclohexane]

Rate = k[1-chloro-1-methylcyclohexane] Rate = k[chloride ion]

Ans: C


Section 5


60. Provide the rate law for the following

reaction. Ans:



Level: Hard

61. Draw a reaction diagram for the following SN1

reaction. Ans:


Section 5 Difficulty Level: Medium 62. Which of the following is a reaction diagram for an SN1 reaction that is

endothermic?


A>B>C>D A>B>D>C D>A>B>C D>C>B>A

Ans: A


Section 5



A. A>B>C>D B. A>B>D>C C. C>A>B>D D. C>D>B>A


reaction. A. A>B>C>D B. A>B>D>C C. D>A>B>C D. D>C>B>A

Ans: A


Section 5



A. A>B>C>D B. A>B>D>C C. C>B>A>D D. D>A>B>C

Ans: C


Section 5

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

68. Provide a mechanism for the following SN1

reaction. Ans:



Level: Easy


following reaction? Ans: D



Level: Easy


following reaction? Ans: B



Level: Easy

71. Which of the following is the product of the following

reaction? Ans: C



Level: Easy




Section 5 Difficulty Level: Medium 73. Provide the product of the following reaction.

74. What is the product of the following reaction. Include

stereochemistry. Ans: Topic: SN1 Mechanism

Section 5


75. What is the product of the following reaction. Include

stereochemistry. Ans: A



Level: Hard 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?

-OH -CH3

-Br

-NH2

Ans: C


Section 6


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

Ans:


Section 6


79. Circle the best leaving group in the following compound.

Ans: Topic: Drawing the Complete SN1 Mechanism

Section 6 Difficulty Level: Easy 80. Which of the following must be protonated in order to be a good leaving group?

Cl Br

NMe2

OH2

Ans: C


Section 6


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

NMe3

I–

OH–

H2S

Ans: D


Section 6


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

83. Which of the following alkyl halides would likely undergo rearrangement during an SN1 reaction?

84. Which of the following is the major product for the following SN1 reaction?

Ans: B


Section 6 Difficulty Level: Medium 85. Draw the anticipated major product for the following reaction.

Ans:


Section 6


86. Draw an energy diagram for the

following reaction. Ans:

Drawing the Complete SN1 Mechanism

Section 6


87. Draw a mechanism for the following

reaction. Ans:


Section 6 Difficulty Level: Hard 88. What is the anticipated major product for the

following reaction? Ans:


Section 6 Difficulty Level: Hard 89. What is the mechanism for the following reaction?

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

Ans:


Section 7 Difficulty Level: Easy

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

SN1 SN2

Protonation

Elimination

Ans: B


Section 7


92. For the following reaction, which of the following is

the product? Ans: D


Section 7 Difficulty Level: Easy 93. For the following reaction, which of the following is the

rate law? k[HBr] k[1-pentanol] k[HBr][1-

pentanol] k[HBr]2

Ans: C


Section 7


94. Draw an energy diagram for the

following reaction. Ans:

Drawing the Complete SN2 Mechanism

Section 7 Difficulty Level: Easy 95. For the following reaction, which of the following is

the mechanism? A. SN1 B. SN2 C. Protonation D. Elimination

96. For the following reaction, which of the following is

the product? Ans: B Topic: Drawing the Complete SN2 Mechanism

Section 7 Difficulty Level: Easy 97. For the following reaction, which of the following is the rate law?

Rate = k[MeI] Rate = k[t-butanol] Rate = k[MeI][t-butanol]

Rate = k[OH]

Ans: C


Section 7


98. Draw an energy diagram for the following reaction.

Ans:


Section 7


99. For the following reaction, provide the mechanism. Ans: Topic: Drawing the Complete SN2 Mechanism

Section 7 Difficulty Level: Medium 100. For the following reaction, draw the product.


Section 7

101. For the following reaction, provide the rate law. Ans:


Section 7


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

Determining Which Mechanism

Section 8 Difficulty Level: Easy 103. What set of reaction conditions should favor an SN2 reaction on 2-

bromo-3methylbutane?

weak nucleophile in a protic solvent weak

nucleophile in an aprotic solvent strong

nucleophile in a protic solvent strong

nucleophile in an aprotic solvent

104. What set of reaction conditions should favor an SN1 reaction on 2-bromo-3methylbutane?

A. weak nucleophile in a protic solvent B. weak nucleophile in an aprotic solvent C. strong nucleophile in a protic solvent D. strong nucleophile in an aprotic solvent

Ans: A

Topic: Determining Which Mechanism

Section 8


105. What reaction mechanism is most likely for substitution on the following compound?


A. SN1 B. SN2 C. Either D. Neither

Ans: B

Topic: Determining Which

Mechanism Section 8

Ans: C


Section 8




Ans: A


Mechanism Section 8 Difficulty Level: Easy 109. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither

Ans: C


Section 8




Ans: D


Mechanism Section 8 Difficulty Level: Easy 111. Is the following nucleophile strong or weak? I–

112. Is the following nucleophile strong or weak? H2O A. Strong

B. Weak C. Not a nucleophile

Ans: B


Section 8


113. Is the following nucleophile strong or weak?

Li+

A. Strong B. Weak C. Not a

nucleophile Ans: C


Mechanism Section 8 Difficulty Level: Easy

114. Is the following nucleophile strong or weak?

HO–


nucleophile Ans: A


Mechanism Section 8 Difficulty Level: Easy 115. Is the following nucleophile strong or weak?

H2S


nucleophile Ans: A


Mechanism Section 8 Difficulty Level: Easy 116. Provide an example of a strong nucleophile.

Ans: There are many possible answers.


Section 8


117. Is the following nucleophile strong or weak? CN–


nucleophile Ans: A


Mechanism Section 8 Difficulty Level: Easy 118. Is the following nucleophile strong or weak?

Na+


nucleophile Ans: C


Mechanism Section 8


119. Why do polar aprotic solvents favor SN2 reactions?

Ans: They raise the energy of the nucleophile, giving a smaller energy of activation for the SN2 pathway. OR They can solvate cations, making the anion more “naked” and thus more nucleophilic.


Section 8


120. What type of solvent would be best for obtaining an optically active product in the following reaction?

polar protic polar

aprotic apolar

aprotic water

Ans: A


Section 8


121. Which of the following leaving groups would you expect to be the best?

Ans: D


Mechanism Section 8 Difficulty Level: Easy 122. Which of the following solvents is not protic?

H2O NH3

hexane

Ans: D

123. What type of solvent is ethanol

(EtOH)? polar aprotic apolar

aprotic polar

protic Ans: C

Topic: Selecting

Reagents Section 9 Difficulty Level: Easy 124. Which reagents would you use for the following reaction?

H2S in water H2S in DMSO

NaSH in water

NaSH in DMSO

Ans: D

Topic: Selecting Reagents

Section 9


125. Which reagents would you use for the following reaction?

HN3 in water

HN3 in acetonitrile

NaN3 in water NaN3

in acetonitrile Ans:


HCl in water

HCl in ether

NaCl in water

NaCl in DMF

Ans: A or B


Section 9



HBr in water

NaBr in water

Ethyl bromide

Ethyl iodide

Ans: C

Topic: Selecting

Reagents Section 9 Difficulty Level: Medium 128. Which reagents would you use for the following reaction?

NaOH in water NaOH in

acetonitrile

Water HCl in

water Ans: C

Topic: Selecting

Reagents Section 9 Difficulty Level: Easy 129. Which reagents would you use for the following reaction?

methanol methanol in acetonitrile

NaOMe in water

NaOMe in acetonitrile

Ans: D


Section 9


130. How would you accomplish the

following transformation? Ans: MeOH (SN1

mechanism) Topic: Selecting Reagents Section 9 Difficulty Level: Medium 131. How would you accomplish the following

transformation? Ans: NaSH in a polar aprotic solvent

Topic: Selecting Reagents Section 9 Difficulty Level: Medium 132. How would you accomplish the

following transformation? Ans: H3CCH2Br

Topic: Selecting

Reagents Section 9 Difficulty Level: Hard 133. How would you accomplish the following transformation?

Ans:


Section 9


134. How would you accomplish the

following transformation? Ans: HBr

Topic: Selecting

Reagents Section 9 Difficulty Level: Medium 135. How would you accomplish the following transformation? Ans: Topic: Selecting

Reagents Section 9 Difficulty Level: Easy 136. Which of the following sets of reagents would best accomplish the following

transformation?

137. Which of the following sets of reagents would best accomplish the following transformation?

Ans: A


Section 9


138. Which of the following sets of reagents would best accomplish the following transformation?

Ans: D

test bank for organic chemistry 1st edition by klein · topic: introduction to substitution section...

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