Ch10 Complete Test Bank Radical Reactions - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package Title: Solomons Test Bank
Course Title: Solomons 13e
Chapter Number: 10
Question type: Multiple Choice
1) Free radicals can be produced by:
A) use of high temperatures.
B) irradiation with light.
C) reaction of a molecule with another free radical.
D) both use of high temperatures and irradiation with light.
E) use of high temperatures, irradiation with light, and reaction of a molecule with another free radical.
Topic: Free Radicals
Section: 10.1
Difficulty Level: Easy
2) As the term "peroxide" is used in Chapter 10, it can refer to which structure(s)?
A) ROOR
B) ROOH
C) 
D) Two of these choices.
E) Three of these choices.
Topic: Miscellaneous
Section: 10.1
Difficulty Level: Easy
3) Which of the following free radicals is the most stable?
A) 
B) 
C) 
D) 
E) 
Topic: Free Radicals
Section: 10.2
Difficulty Level: Easy
4) Hydrogen atom abstraction from which position would yield the most stable free radical intermediate during the reaction of bromine with 2,2,3-trimethylpentane?
A) C1
B) C2
C) C3
D) C4
E) C5
Topic: Free Radicals
Section: 10.2
Difficulty Level: Easy
5) Which of these molecules is not expected to arise as a product of the high temperature chlorination of methane?
A) CCl4
B) HCCl3
C) CH2Cl2
D) CH3CH3
E) CH2=CH2
Topic: Reaction Products
Section: 10.3
Difficulty Level: Easy
6) A chain reaction is one that:
A) involves a series of steps.
B) involves two steps of equal activation energy.
C) is one that can be initiated by light.
D) involves a series of steps, each of which generates a reactive intermediate that brings about the next step.
E) involves free radicals that have an unusual stability and thereby cause a large quantum yield.
Topic: Mechanisms
Section: 10.4
Difficulty Level: Easy
7) Which of the following gas-phase reactions is a possible chain-terminating step in the light-initiated chlorination of methane?
A) Cl–Cl 2Cl·
B) Cl· + CH4 CH3· + H–Cl
C) CH3· + CH3· CH3–CH3
D) CH3· + Cl–Cl CH3Cl + Cl·
E) More than one of these choices.
Topic: Mechanisms
Section: 10.4
Difficulty Level: Easy
8) In the presence of light, ethane (1 mol) reacts with chlorine (1 mol) to form which product(s)?
A) CH2ClCHCl2
B) CH3CHCl2
C) CH3CH2Cl
D) ClCH2CH2Cl
E) All of these choices.
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5
Difficulty Level: Medium
9) How many different monochlorobutanes (including stereoisomers) are formed in the free radical chlorination of butane?
A) 1
B) 2
C) 3
D) 4
E) 5
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5
Difficulty Level: Medium
10) The reaction of 2-methylbutane with chlorine and light would yield how many monochloro derivatives? (include stereoisomers)
A) 2
B) 3
C) 4
D) 5
E) 6
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5
Difficulty Level: Medium
11) If chlorocyclopentane were chlorinated to form all possible dichloro compounds and the product mixture subjected to precise fractional distillation, how many fractions would be obtained (ideally)?
A) 3
B) 4
C) 5
D) 7
E) 9
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5
Difficulty Level: Medium
12) At some temperatures, the relative reactivities of 3°, 2° and 1° alkane hydrogens in free radical chlorination are in the ratio of 5:3:1. Thus, monochlorination of isopentane should produce these percentages of 2-chloro-2-methylbutane (A), combined 1-chloro-2-methylbutane and 1-chloro-3-methylbutane (B), and 2-chloro-3-methylbutane (C):
A) 8% A, 75% B, 17% C
B) 25% A, 45% B, 30% C
C) 29% A, 44% B, 18% C
D) 30% A, 35% B, 35% C
E) 36% A, 43% B, 21% C
Topic: Free Radicals
Section: 10.5
Difficulty Level: Hard
13) What feature would you expect to see in the 1H NMR spectrum of B after subjecting A to the following reaction?
A) There would be only 4 aromatic protons at low field.
B) The signal for the protons on the benzylic carbon would be a doublet.
C) The signal for the methyl protons would be a triplet.
D) The signal for the methyl protons would be a doublet.
E) The signal for the methyl protons would integrate for only 2 hydrogens.
Topic: Proton NMR- Chemical Shift, Splitting, Etc.
Section: 9.2, 10.5
Difficulty Level: Medium
14) In a competition reaction, equimolar amounts of five alkanes compete for a deficiency of chlorine at 300 °C. The greatest amount of reaction would occur in the case of which of these alkanes?
A) Ethane
B) Propane
C) Butane
D) Isobutane
E) Pentane
Topic: Reaction Products
Section: 10.3, 10.5
Difficulty Level: Medium
15) What sequence of reactions could be used to prepare cis-1,2-cyclopentanediol from cyclopentane?
A) (1) Cl2, h; (2) t-BuOK/t-BuOH; (3) OsO4; (4) NaHSO3/H2O
B) (1) t-BuOK/t-BuOH; (2) Cl2, h; (3) NaOH/H2O
C) (1) Cl2, h; (2) t-BuOK/t-BuOH; (3) H2O2
D) (1) NaOH/H2O; (2) Br2; (3) NaNH2 (2 eq.)/liq. NH3; (4) KMnO4, NaOH/H2O, 5 °C
E) (1) Cl2, h; (2) t-BuOK/t-BuOH; (3) Hg(OAc)2, H2O (4) NaBH4, H3O+
Topic: Reaction Products
Section: 6.18, 8.16, 10.5
Difficulty Level: Hard
16) Select the structure of the major product formed in the following reaction.
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
17) In the presence of light at 25 °C, isobutane (1 mol) and bromine (1 mol) yield which monobromo product(s)?
A) 2-Methyl-1-bromopropane (almost exclusively)
B) 2-Methyl-2-bromopropane (almost exclusively)
C) A mixture of 50% (A) and 50% (B)
D) A mixture of 90% (A) and 10% (B)
E) Butyl bromide
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
18) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
19) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
20) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
21) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
22) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
23) Mono-bromination of the following alkane, 
, (using Br2 with light) would give?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.5
Difficulty Level: Easy
24) Which hydrogen would be abstracted first when mono-brominating with Br2 and light?
A) Ha
B) Hb
C) Hc
D) Hd
E) He
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
25) Which hydrogen would be abstracted first when mono-brominating with Br2 and light?
A) Ha
B) Hb
C) Hc
D) Hd
E) He
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
26) Which hydrogen would be abstracted first when mono-brominating with Br2 and light?
A) Ha
B) Hb
C) Hc
D) Hd
E) He
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
27) Which hydrogen would be abstracted first when mono-brominating with Br2 and light?
A) Ha
B) Hb
C) Hc
D) Hd
E) He
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
28) Which hydrogen would be abstracted first when mono-brominating with Br2 and light?
A) Ha
B) Hb
C) Hc
D) Hd
E) He
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
29) Free radical mono-halogenation of an alkane is typically conducted using bromine versus chlorine because
A) the bromine radical is more reactive and therefore more selective.
B) the chlorine radical is more reactive and therefore more selective.
C) the chlorine radical is less reactive and therefore more selective.
D) the bromine radical is less reactive and therefore more selective.
E) None of these choices.
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
30) Which statement best describes the reaction of bromine with isobutane?
A) Bromine radical selectively abstracts the tertiary hydrogen.
B) The transition state of the rate determining step is product-like.
C) The major product formed from this reaction is 1-bromo-2-methylpropane.
D) Bromine radical selectively abstracts the tertiary hydrogen and the transition state of the rate determining step is product-like.
E) Bromine radical selectively abstracts the tertiary hydrogen, the transition state of the rate determining step is product-like, and the major product formed from this reaction is 1-bromo-2-methylpropane.
Topic: Mechanisms
Section: 10.5
Difficulty Level: Medium
31) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.10, 10.5
Difficulty Level: Medium
32) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.17, 10.5
Difficulty Level: Medium
33) What is the product for the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.10, 7.8, 10.5
Difficulty Level: Medium
34) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.5
Difficulty Level: Medium
35) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.5
Difficulty Level: Medium
36) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.5
Difficulty Level: Medium
37) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.5
Difficulty Level: Medium
38) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.5
Difficulty Level: Medium
39) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 4.16, 6.18, 10.5
Difficulty Level: Hard
40) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 4.16, 7.11, 10.5
Difficulty Level: Hard
41) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 7.11, 10.5
Difficulty Level: Hard
42) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.6, 10.5
Difficulty Level: Hard
43) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.6, 10.5
Difficulty Level: Hard
44) What is the major product obtained from the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Multistep Reactions
Section: 6.18, 8.6, 10.5
Difficulty Level: Hard
45) What is the final product, C, obtained via the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Multistep Reactions
Section: 6.18, 8.7, 10.5
Difficulty Level: Hard
46) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.7, 10.5
Difficulty Level: Hard
47) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.12, 10.5
Difficulty Level: Hard
48) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.12, 10.5
Difficulty Level: Hard
49) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.12, 10.5
Difficulty Level: Hard
50) The hybridization state of the carbon of a methyl radical is:
A) sp
B) sp2
C) sp3
D) sp4
E) p3
Topic: Free Radicals
Section: 10.6
Difficulty Level: Easy
51) The p orbital of a methyl radical carbon, CH3·, contains how many electrons?
A) 1
B) 2
C) 3
D) 4
E) 0
Topic: Free Radicals
Section: 10.6
Difficulty Level: Easy
52) The reaction of 2,2-dimethylbutane with chlorine would yield how many monochloro derivatives? (include stereoisomers)
A) 1
B) 2
C) 3
D) 4
E) 5
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
53) The free radical chlorination of pentane produces this number of monochloro compounds, including stereoisomers.
A) 2
B) 3
C) 4
D) 5
E) 6
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
54) The reaction between cyclopropane and one equivalent of bromine when exposed to light would yield how many different compounds (including stereoisomers)?
A) 1
B) 2
C) 3
D) 4
E) 5
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
55) Free radical chlorination will produce but one monochloro derivative in the case of:
A) Propane
B) Butane
C) Isobutane
D) Isopentane
E) Neopentane
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
56) Free radical chlorination of hexane produces this number of monochloro derivatives (including stereoisomers):
A) 3
B) 4
C) 5
D) 7
E) 8
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
57) More than one monochloro compound can be obtained from the free radical chlorination of:
A) Cyclopentane
B) Neopentane
C) Isobutane
D) Ethane
E) Methane
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
58) What is the total number of trichloropropanes which can be produced by free radical chlorination of propane? Include all stereoisomers.
A) 4
B) 5
C) 6
D) 7
E) 8
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
59) The free radical chlorination of (R)-2-chloropentane forms a mixture of dichloropentanes which includes:
A) three optically active compounds.
B) two achiral compounds.
C) two meso compounds.
D) one pair of diastereomers.
E) one racemic mixture.
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Hard
60) How many monochloro derivatives, including stereoisomers, can be formed in the chlorination of 1-bromobutane?
A) 4
B) 5
C) 6
D) 7
E) 8
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
61) The free radical chlorination of 3-chloropentane forms a mixture of dichloropentanes which, on precise fractional distillation, affords these fractions:
A) 4 fractions, none optically active
B) 4 fractions, 2 optically active
C) 7 fractions, 4 optically active
D) 7 fractions, 6 optically active
E) 7 fractions, all optically active
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Hard
62) Consider the light-initiated chlorination of (S)-2-chlorobutane followed by careful fractional distillation (or separation by GLC) of all of the products with the formula C4H8Cl2. How many fractions (in total) would be obtained and how many of these fractions would be optically active?
A) Three fractions total; all optically active
B) Four fractions total; three fractions optically active
C) Five fractions total; all optically active
D) Five fractions total; four fractions optically active
E) Five fractions total; three fractions optically active
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Hard
63) Which free radical would be most stable?
A) 
B) 
C) 
D) 
E) 
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
64) Which free radical would be least stable?
A)
B)
C)
D)
E)
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
65) Which free radical would be most stable?
A) 
B) 
C) 
D) 
E) 
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
66) Which free radical would be most stable?
A) I
B) II
C) III
D) IV
E) V
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
67) Which free radical would be least stable?
A) I
B) II
C) III
D) IV
E) V
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
68) Which hydrogen atom(s) of 
is/are most susceptible to abstraction by free radicals?
A) I
B) II
C) III
D) IV
E) V
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
69) Which hydrogen atom(s) of 
is/are most susceptible to abstraction by free radicals?
A) I
B) II
C) III
D) IV
E) V
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
70) Which hydrogen atom(s) of 
is/are least susceptible to abstraction by free radicals?
A) I
B) II
C) III
D) IV
E) V
Topic: Stability (Alkenes, Cations, Radicals)
Section: 10.8
Difficulty Level: Easy
71) Which set of conditions does not result in allylic halogenation of an alkene?
A) Cl2 at 400 C
B) Cl2 in CCl4 at 25 C
C) Cl2, ROOR, h
D) Br2 at low concentration in CCl4
E) N-Bromosuccinimide in CCl4, ROOR
Topic: Allylic Halogenation
Section: 10.8
Difficulty Level: Medium
72) Which carbon of 
is predicted to be the major site of substitution when this alkene reacts with chlorine at 400 C?
A) I
B) II
C) III
D) IV
E) V
Topic: Allylic Halogenation
Section: 10.8
Difficulty Level: Medium
73) Which would be the best synthesis to produce the vicinal dibromide?
A) 
B) 
C) 
D) 
E) 
Topic: Multistep Reactions
Section: 10.8
Difficulty Level: Medium
74) Which of the following compounds is not formed as a result of a chain-termination step in the free radical chlorination of propene?
A) CH2=CHCH2Cl
B) Cl2
C) CH2=CHCH2CH2CH=CH2
D) HCl
E) All can be formed in chain-termination steps.
Topic: Allylic Halogenation
Section: 10.8
Difficulty Level: Hard
75) An unsaturated product results from the reaction of cyclohexene with which of these?
A) Br2/CCl4 at 25 C
B) NBS/CCl4, ROOR
C) HCl, ROOR
D) HCl, no peroxides
E) More than one of these choices.
Topic: Allylic Halogenation
Section: 10.8
Difficulty Level: Medium
76) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.9
Difficulty Level: Hard
77) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.10, 10.9
Difficulty Level: Hard
78) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.9
Difficulty Level: Hard
79) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.9
Difficulty Level: Hard
80) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.9
Difficulty Level: Hard
81) Which of the following would be the major product in the following reaction sequence?
A) I
B) II
C) III
D) two of these choices
E) none of these choices
Topic: Reaction Products
Section: 6.5, 10.9
Difficulty Level: Hard
82) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.17, 10.9
Difficulty Level: Hard
83) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.16, 10.9
Difficulty Level: Hard
84) What is the product for the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.17, 10.9
Difficulty Level: Hard
85) What would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.10
Difficulty Level: Easy
86) What product would result from the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 10.10
Difficulty Level: Easy
87) The reaction of 1-butene with HBr in the presence of peroxides yields 1-bromobutane. The mechanism for the reaction involves:
A) attack on the alkene by a Br+ ion.
B) attack on the alkene by a H+ ion.
C) attack on the alkene by a bromine atom, Br·.
D) attack on the alkene by a hydrogen atom, H·.
E) isomerization of the 2-bromobutane produced initially.
Topic: Mechanisms
Section: 10.10
Difficulty Level: Easy
88) Which of the following would serve as the best synthesis of 2-bromohexane?
A) 
B) 
C) 
D) 
E) All of these choices would be equally suitable.
Topic: Synthesis
Section: 10.10
Difficulty Level: Medium
89) Which of the following combinations of reactants can provide a demonstrable example of anti-Markovnikov addition?
A) CH2=CHCH3 + HCl + ROOR
B) CH3CH=CH2 + H2O + Cl2
C) CH3CH=CHCH3 + HBr + ROOR
D) CH3CH2CH=CH2 + HBr + ROOR
E) CH3CH2CH=CH2 + Br2 + ROOR
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium
90) 2-Methyl-2-butene reacts with HBr in the presence of peroxide to give (chiefly):
A) (CH3)2CHCH2CH2Br
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium
91) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.10
Difficulty Level: Medium
92) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.10
Difficulty Level: Medium
93) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.10, 10.10
Difficulty Level: Medium
94) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Medium
95) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Medium
96) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 10.10
Difficulty Level: Hard
97) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.2, 10.10
Difficulty Level: Hard
98) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Medium
99) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Medium
100) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Medium
101) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Hard
102) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Hard
103) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.18, 10.10
Difficulty Level: Hard
104) What would be the major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 6.5, 10.10
Difficulty Level: Hard
105) Which would be the best way to carry out the following synthesis?
A) (1) HA, heat; (2) HBr
B) (1) HBr and peroxides; (2) Br2/CCl4
C) (1) HA, heat; (2) HBr and peroxides
D) (1) Br2/CCl4; (2) HA, heat
E) (1) HA, heat; (2) Br2/CCl4
Topic: Synthesis
Section: 7.7, 10.10
Difficulty Level: Medium
106) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.5, 7.15, 10.10
Difficulty Level: Hard
107) Carbocations are NOT intermediates in which one of the following reactions?
A) 
B) 
C) 
D) 
E) More than one of these choices.
Topic: Mechanisms
Section: 7.7, 8.2, 8.4, 10.10
Difficulty Level: Medium
108) What is the major product obtained from the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Multistep Reactions
Section: 6.18, 8.7, 10.10
Difficulty Level: Hard
109) What is the product for the following three-step reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Synthesis
Section: 6.18, 8.15, 10.10
Difficulty Level: Hard
110) What is the major product obtained from the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Multistep Reactions
Section: 6.5, 6.18, 10.6, 10.10
Difficulty Level: Hard
111) What is the major product obtained from the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Topic: Multistep Reactions
Section: 6.5, 6.18, 10.5, 10.10
Difficulty Level: Hard
112) If propene polymerization is initiated by the use of diacyl peroxide, this is an intermediate species formed early in the process.
A) 
B) 
C) 
D) 
E) 
Topic: Miscellaneous
Section: 10.11
Difficulty Level: Medium
113) According to the present explanation of the role of atmospheric chlorofluorocarbons in ozone depletion, it is this species which destroys, i.e., reacts irreversibly with, ozone.
A) F
B) Cl
C) O
D) ClO
E) FO
Topic: Miscellaneous
Section: 10.12
Difficulty Level: Medium
Question type: True/False
114) Radical chlorinations are for the most part not synthetically practical due to high reactivity of the chlorine radical.
Topic: Reaction Products
Section: 10.3
Difficulty Level: Easy
115) The terms “chain reaction” refer to a process where a long sequence of various intermediates are generated to arrive at the formation of a single product.
Topic: Mechanisms
Section: 10.4
Difficulty Level: Easy
116) Hydrogen abstraction from methane via a radical reaction generates a species that has trigonal planar geometry.
Topic: Free Radicals
Section: 10.6
Difficulty Level: Easy
117) Tertiary carbon radicals are the most stable carbon radical that can be generated from hydrogen abstraction.
Topic: Radical Stability
Section: 10.9
Difficulty Level: Hard
118) Compared to bromine, N-bromosuccinimide is a superior reagent for radical bromination of allylic carbons, as there is minimal production of vicinal dibromides.
Topic: Synthesis
Section: 10.9
Difficulty Level: Hard
119) The end result of the autoxidation processes is the formation of water molecules as oxygen in the air extracts hydrogen from various sources.
Topic: Autoxidation
Section: 10.12
Difficulty Level: Medium
Question type: fill-in-the-blank
120) Intermediates possessing unpaired electrons are called ___.
Topic: General
Section: 10.1
Difficulty Level: Easy
121) A covalent bond breaking so that each of the resulting intermediates bears a single unpaired electron is an example of ___ bond cleavage.
Topic: General
Section: 10.1
Difficulty Level: Easy
122) Although alkyl radicals are uncharged, the carbon bearing the odd electron is electron ___, and alkyl groups provide a ___ effect.
Topic: General
Section: 10.2
Difficulty Level: Medium
123) The mechanism for a free-radical reaction consists of three types of steps. These are: ___.
Topic: General
Section: 10.4
Difficulty Level: Easy
124) In a chain-initiating step, radicals are ___.
Topic: General
Section: 10.4
Difficulty Level: Easy
125) In a chain-terminating step, radicals are ___.
Topic: General
Section: 10.4
Difficulty Level: Easy
126) In a chain-propagating step, one radical ___.
Topic: General
Section: 10.4
Difficulty Level: Easy
Question type: Essay
127) Provide a reasonable mechanistic explanation for the formation of small amounts of 3,3,4,4-tetramethylhexane during the free-radical bromination of 2-methylbutane.
Topic: Mechanisms
Section: 10.4
Difficulty Level: Medium
128) Briefly, but clearly, explain the following observation:
When 2-methylbutane reacts with Cl2/h, the monochlorinated products consist of four constitutional isomers in significant yields. However, when the same alkane is allowed to react with Br2/ h, there is only one major monobromination product.
Topic: Reactivity / Selectivity
Section: 10.5
Difficulty Level: Medium
129) Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.
Topic: Multistep Reactions
Section: 6.18, 8.7, 10.5
Difficulty Level: Hard
130) Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.
Topic: Multistep Reactions
Section: 6.18, 8.17, 10.5
Difficulty Level: Hard
131) Draw bond-line formulas of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl2 under UV irradiation. For each structure, indicate, with an asterisk, any stereocenters that might be present.
Topic: Reaction Products (Isomers)
Section: 10.6, 10.7
Difficulty Level: Medium
132) Draw bond-line formulas of all monochloro derivatives that might be formed when 1,1-dimethylcyclobutane is allowed to react with Cl2 under UV irradiation. For each structure, indicate, with an asterisk, any stereocenters that might be present.
Topic: Reaction Products (Isomers)
Section: 10.6, 10.7
Difficulty Level: Medium
133) Draw bond-line formulas of all monochloro derivatives that might be formed when 3-ethylhexane is allowed to react with Cl2 under UV irradiation. For each structure, indicate, with an asterisk, any stereocenters that might be present.
Topic: Reaction Products (Isomers)
Section: 10.6, 10.7
Difficulty Level: Medium
134) Deduce the structure of a substance, C8H18, which gives only a single monochloro derivative upon reaction with Cl2 under UV irradiation.
Topic: Structure Elucidation
Section: 10.6, 10.7
Difficulty Level: Medium
135) Draw bond-line formulas of all dichloro derivatives that might be formed when 1-chloro-2,2,3,3-tetramethylpentane is allowed to react with Cl2 under UV irradiation. For each structure, indicate, with an asterisk, any stereocenters that might be present.
Topic: Reaction Products (Isomers)
Section: 10.6, 10.7
Difficulty Level: Medium
136) Draw bond-line formulas of all monochloro derivatives that might be formed when 2,2,4-trimethylpentane is allowed to react with Cl2 under UV irradiation. For each structure, indicate, with an asterisk, any stereocenters that might be present.
Topic: Reaction Products (Isomers)
Section: 10.6, 10.7
Difficulty Level: Medium
137) Briefly explain why when cyclopentene is treated with Br2 that trans-1,2-dibromocyclopentane is the major product at high temperatures but at low temperatures, racemic 3-bromocyclopentene is the major product.
Topic: Mechanisms
Section: 8.11, 10.8
Difficulty Level: Medium
138) Determine the identification of compounds W, X, Y and Z using the structural information shown below.
Topic: Structural Identification
Section: 6.18, 8.15, 9.2, 10.8
Difficulty Level: Hard
139) Develop a synthetic strategy for 1-phenylpropyne from ethyl benzene. Start by writing the retrosynthesis analysis and then write the reactions as needed.
Topic: Retrosynthetic Analysis
Section: 7.11, 10.9
Difficulty Level: Hard
Question type: fill-in-the-blank
140) The reason why ___ and ___ radicals are more stable than alkyl radicals is due to electron delocalization through resonance.
Topic: General
Section: 10.8, 10.9
Difficulty Level: Easy
141) While the electrophilic addition of HBr to an alkene is ionic and follows Markovnikov's rule, if the reaction is done in the presence of peroxides it becomes a ___ reaction and is ___ in regiochemistry.
Topic: General
Section: 10.10
Difficulty Level: Easy
142) Unsymmetrical alkenes give Markovnikov products through the most stable ___ intermediates and anti-Markovnikov products through the most stable ___ intermediates.
Topic: General
Section: 10.10
Difficulty Level: Medium
Question type: Essay
143) What product(s) might be obtained via chain-termination step(s) during the reaction of 2-methylpropene with HBr in presence of peroxides?
Topic: Mechanisms
Section: 10.4, 10.10
Difficulty Level: Medium
144) Suggest a reasonable strategy for the synthesis of 1-bromo-2-methylcyclohexane from methylcyclohexane.
Topic: Multistep Synthesis
Section: 6.18, 10.6, 10.10
Difficulty Level: Hard
145) Suggest a strategy for converting 1-methylcyclohexene into 1-cyclohexylmethanol.
Topic: Multistep Synthesis
Section: 6.18, 8.8, 10.6, 10.10
Difficulty Level: Hard
146) Complete the following reaction sequence: indicate regiochemical/stereochemical details as relevant.
Topic: Multistep Reactions
Section: 6.5, 6.18, 10.5, 10.10
Difficulty Level: Hard
Question type: fill-in-the-blank
147) Macromolecules made up of many repeating subunits are called ___.
Topic: General
Section: 10.11
Difficulty Level: Easy
148) Two radicals that are very important in biological processes are ___ and ___.
Topic: General
Section: 10.12
Difficulty Level: Medium
149) Chlorofluorocarbons, or freons, diffuse into the upper atmosphere. There, ultraviolet light initiates a radical chain reaction that has been shown to cause extreme damage to ___.
Topic: General
Section: 10.12
Difficulty Level: Easy
150) Free radical mono-halogenation of an alkane is typically conducted using bromine versus chlorine because
A) the bromine radical is more reactive and therefore less selective.
B) the chlorine radical is more reactive and therefore less selective.
C) the chlorine radical is less reactive and therefore less selective.
D) the bromine radical is less reactive and therefore less selective.
E) None of these choices.
Topic: Reaction Products
Section: 10.5
Difficulty Level: Medium
151) The unpaired electron on the carbon of a methyl radical is contained in which orbital:
A) sp
B) sp2
C) sp3
D) s
E) p
Topic: Free Radicals
Section: 10.6
Difficulty Level: Easy
152) The free radical chlorination of methylcyclopropane produces this number of monochloro compounds, including stereoisomers.
A) 2
B) 3
C) 4
D) 5
E) 6
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
153) Free radical chlorination will produce but two monochloro derivatives, including stereoisomers, in the case of:
A) Propane
B) Butane
C) Isobutane
D) Isopentane
E) More than one of these choices.
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
154) Free radical chlorination will produce but three monochloro derivatives, including stereoisomers, in the case of:
A) Propane
B) Butane
C) Isobutane
D) Isopentane
E) More than one of these choices.
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
155) Free radical chlorination will produce but four monochloro derivatives, including stereoisomers, in the case of:
A) Isobutane
B) Butane
C) Pentane
D) Isopentane
E) More than one of these choices.
Topic: Reaction Products (Isomers)
Section: 10.3, 10.5, 10.7
Difficulty Level: Medium
156) What is the major product of the following reaction?
A) 1-bromohexane
B) 2-bromohexane
C) 3-bromohexane
D) 1,2-dibromohexane
E) 2-bromohexanol
Topic: Synthesis
Section: 10.10
Difficulty Level: Medium
157) What is the major product of the following reaction?
A) 1-bromohexane
B) 2-bromohexane
C) 3-bromohexane
D) 1,2-dibromohexane
E) 2-bromohexanol
Topic: Synthesis
Section: 10.10
Difficulty Level: Medium
158) What is the major product of the following reaction?
CH2=CHCH3 + HCl + ROOR
A) 1-chloropropane
B) 1-chloro-2-propanol
C) 2-chlorobutane
D) 1-chlorobutane
E) None of these choices.
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium
159) What is the major product of the following reaction?
CH3CH=CH2 + H2O + Cl2
A) 1-chloropropane
B) 1-chloro-2-propanol
C) 2-chlorobutane
D) 1-chlorobutane
E) None of these choices.
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium
160) What is the major product of the following reaction?
CH3CH=CHCH3 + HCl + ROOR
A) 1-chloropropane
B) 1-chloro-2-propanol
C) 2-chlorobutane
D) 1-chlorobutane
E) None of these choices.
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium
161) What is the major product of the following reaction?
CH3CH2CH=CH2 + HCl + ROOR
A) 1-chloropropane
B) 1-chloro-2-propanol
C) 2-chlorobutane
D) 1-chlorobutane
E) None of these choices.
Topic: Reaction Products
Section: 10.10
Difficulty Level: Medium