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
Trang 1Test Bank for Organic Chemistry 1st Edition by Klein
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
Trang 25 Draw an example of a substitution reaction
Ans: Numerous options!
Topic: Introduction to Substitution
Section 1
Difficulty Level: Easy
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
Topic: Introduction to Substitution
Section 1
Difficulty Level: Easy
8 What is the leaving group in the following
Trang 39 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:
Topic: Introduction to Substitution
Section 1
Difficulty Level: Easy
11 What is the nucleophile in the following
reaction? Ans: A
Topic: Introduction to Substitution
Section 1
Difficulty Level: Easy
12 What is the electrophile in the following reaction?
Ans: B
Topic: Introduction to Substitution
Section 1
Difficulty Level: Easy
13 What is the leaving group in the following
reaction? Sulfur
Carbon
Trang 4Difficulty Level: Easy
14 Which of the following is the correct IUPAC name of the following structure? Chlorocyclopentane
Trang 516 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
Difficulty Level: Easy
18 Which of the following is the correct structure for a compound with the
IUPAC name of 1-iodo-3-ethylcyclohexane?
Ans: B
Topic: Alkyl Halides
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
Topic: Alkyl Halides
Trang 6Section 2
Difficulty Level: Easy
20 Which of the following compounds has a tertiary
carbon? Ans: B
Topic: Alkyl Halides
Section 2 Difficulty
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:
Topic: Alkyl Halides
Section 2
Difficulty Level: Medium
24 Identify the labeled carbon as primary, secondary, or tertiary
Trang 7Ans: tertiary
Topic: Alkyl Halides
Section 2
Difficulty Level: Easy
25 Identify the labeled carbon as primary, secondary, or
tertiary Ans: primary
Topic: Alkyl Halides
Section 2 Difficulty
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
Trang 8It is a substitution reaction
Ans: C
Topic: Possible Mechanisms
Section 3
Difficulty Level: Hard
29 Provide examples of the 4 patterns for steps in the mechanisms of
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:
Trang 9Topic: Possible Mechanisms
Section 3
Difficulty Level: Easy
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? 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
Topic: Possible Mechanisms
Section 3
Difficulty Level: Easy
35 Which of the following shows the correct arrow for loss of a bromide leaving group?
Ans: A
Trang 10Topic: Possible Mechanisms
Section 3
Difficulty Level: Hard
36 Provide an arrow-pushing mechanism for the following
Difficulty Level: Easy
39 Which of the following is the product of the following SN2 reaction?
Trang 11Ans: C
Topic: SN2 Mechanism
Section 4
Difficulty Level: Hard
40 Which of the following is the product of the following SN2 reaction? Ans: C
Topic: SN2 Mechanism
Section 4
Difficulty Level: Medium
41 Provide the SN2 product of the following reaction
42 Provide a mechanism for this
reaction Ans:
Topic: SN2 Mechanism
Section 4
Difficulty Level: Easy
43 Which of the following is a mechanism for an SN2
reaction? Ans: C
Show arrows more carefully in B, C,
D Topic: SN2 Mechanism
Section 4
Trang 12Difficulty Level: Easy
44 Which of the following is the product of the following
reaction? Ans: A
Topic: SN2 Mechanism
Section 4
Difficulty Level: Easy
45 Which of the following is the product of the following
reaction? Ans: D
Topic: SN2 Mechanism
Section 4
Difficulty Level: Easy
46 Which of the following is the product of the following reaction? Ans: A
Topic: SN2 Mechanism
Section 4
Difficulty Level: Medium
47 What is the product of the following reaction?
48 What is the product of the following
reaction? Ans:
Topic: SN2 Mechanism
Trang 13Section 4
Difficulty 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
Difficulty Level: Easy
51 Rank the following substrates from most to least reactive in an SN2 reaction A A>B>C>D
Trang 14Section 4
Difficulty Level: Easy
52 Rank the following substrates from most to least reactive in an SN2 reaction A A>B>C>D
Difficulty Level: Easy
53 Rank the following substrates from most to least reactive in an SN2 reaction A A>B>C>D
Difficulty Level: Hard
54 Draw a reaction diagram for the following reaction
Ans:
Topic: SN2 Mechanism
Section 4
Trang 15Difficulty 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?
57 Given the following rate law, what will happen to the rate if the concentration
of both reactants is doubled?
A It will be doubled
B It will not change
C It will decrease in half
D It will increase 4-fold
Trang 16Ans: D
Topic: SN2 Mechanism
Section 4
Difficulty 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
Topic: SN1 Mechanism
Section 5
Difficulty Level: Easy
59 Which of the following is the rate law for the following
reaction? Rate = k[H2O]
Rate = k[H2
O][1-chloro-1-methylcyclohexane] Rate =
k[1-chloro-1-methylcyclohexane] Rate = k[chloride ion]
Trang 1760 Provide the rate law for the following
reaction Ans:
Topic: SN1 Mechanism
Section 5
Difficulty Level: Hard
61 Draw a reaction diagram for the following SN1 reaction
Ans:
Topic: SN1 Mechanism
Section 5
Difficulty Level: Medium
62 Which of the following is a reaction diagram for an SN1 reaction that
Trang 18Difficulty Level: Easy
64 Rank the following substrates from most to least reactive in an SN1 reaction A A>B>C>D
Difficulty Level: Easy
65 Rank the following substrates from most to least reactive in an SN1 reaction A A>B>C>D
Difficulty Level: Easy
66 Rank the following substrates from most to least reactive in an SN1 reaction A A>B>C>D
B A>B>D>C
C C>B>A>D
D D>A>B>C
Trang 19Ans: C
Topic: SN1 Mechanism
Section 5
Difficulty Level: Hard
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:
Topic: SN1 Mechanism
Section 5
Difficulty Level: Easy
69 Which of the following is the product of the following
reaction? Ans: D
Topic: SN1 Mechanism
Section 5
Difficulty Level: Easy
70 Which of the following is the product of the following
reaction? Ans: B
Topic: SN1 Mechanism
Section 5
Trang 20Difficulty Level: Easy
71 Which of the following is the product of the following
reaction? Ans: C
Topic: SN1 Mechanism
Section 5
Difficulty Level: Easy
72 Which of the following is the product of the following reaction?
Ans: A
Topic: SN1 Mechanism
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
Difficulty Level: Easy
75 What is the product of the following reaction Include stereochemistry Ans: A
Topic: SN1 Mechanism
Trang 21Section 5
Difficulty 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
Difficulty Level: Easy
77 Which of the following is a good leaving
Difficulty Level: Medium
78 What is the best leaving group in the following compound?
Ans:
Topic: Drawing the Complete SN1 Mechanism
Section 6
Difficulty Level: Medium
79 Circle the best leaving group in the following compound
Trang 22Ans:
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?
Trang 2382 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
Topic: Drawing the Complete SN1 Mechanism
Section 6
Difficulty Level: Medium
85 Draw the anticipated major product for the following reaction
86 Draw an energy diagram for the following
reaction Ans:
Trang 24Topic: Drawing the Complete SN1 Mechanism
Section 6
Difficulty Level: Hard
87 Draw a mechanism for the following
reaction Ans:
Topic: Drawing the Complete SN1 Mechanism
Section 6
Difficulty Level: Hard
88 What is the anticipated major product for the following reaction? Ans:
Topic: Drawing the Complete SN1 Mechanism
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:
Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Easy
91 For the following reaction, which of the following is the mechanism?
Trang 25Difficulty Level: Easy
92 For the following reaction, which of the following is the product? Ans: D
Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Easy
93 For the following reaction, which of the following is the rate law? k[HBr]
Trang 26Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Easy
95 For the following reaction, which of the following is the
Difficulty Level: Easy
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
Trang 27Section 7
Difficulty Level: Medium
98 Draw an energy diagram for the following
reaction Ans:
Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Hard
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
Ans:
Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Medium
101 For the following reaction, provide the rate law
Ans:
Topic: Drawing the Complete SN2 Mechanism
Section 7
Difficulty Level: Medium
102 For the following reaction, provide an energy diagram Ans:
Trang 28Topic: Determining Which Mechanism
Section 8
Difficulty Level: Easy
103 What set of reaction conditions should favor an SN2 reaction on 3-methylbutane?
2-bromo-weak nucleophile in a protic solvent
weak nucleophile in an aprotic solvent
strong nucleophile in a protic solvent
strong nucleophile in an aprotic solvent
Ans: D
104 What set of reaction conditions should favor an SN1 reaction on 3-methylbutane?
2-bromo-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
105 What reaction mechanism is most likely for substitution on the
following compound?
Trang 29Difficulty Level: Easy
106 What reaction mechanism is most likely for substitution on the following compound?
Trang 30Ans: C
Topic: Determining Which Mechanism
Section 8
Difficulty Level: Easy
108 What reaction mechanism is most likely for substitution on the following compound?
Trang 31110 What reaction mechanism is most likely for substitution on the following compound?
Trang 32Ans: B
Topic: Determining Which Mechanism
Section 8
Difficulty Level: Easy
113 Is the following nucleophile strong or weak?
Difficulty Level: Easy
114 Is the following nucleophile strong or weak?
Difficulty Level: Easy
115 Is the following nucleophile strong or weak? H2S
Trang 33Difficulty Level: Easy
116 Provide an example of a strong nucleophile Ans: There are many possible answers
Topic: Determining Which Mechanism
Section 8
Difficulty Level: Easy
117 Is the following nucleophile strong or weak?
Difficulty Level: Easy
118 Is the following nucleophile strong or weak?
Na+
A Strong
Trang 34Difficulty Level: Hard
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
Topic: Determining Which Mechanism
Section 8
Difficulty Level: Medium
120 What type of solvent would be best for obtaining an optically active product
in the following reaction?
Difficulty Level: Easy
121 Which of the following leaving groups would you expect to be the
best? Ans: D