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Essential Organic Chemistry
Essential Organic Chemistry
Chapter 5
1)
The relatively loosely held electrons of the carbon-carbon double bond attack an electrophile to begin the reaction.
Section: 5.0
2)
Complete the following reaction and provide a detailed, step-by-step mechanism for the process.
Answer:
Section: 5.1
3)
Answer:
Essential Organic Chemistry (Bruice)
Chapter 5
4)
A)
I
B)
II
C)
III
D)
IV
E)
V
Answer:
D
Section: 5.2
Essential Organic Chemistry (Bruice)
Chapter 5
5)
Which of the following alkenes reacts with HCl at the slowest rate?
A)
B)
C)
D)
E)
Answer:
A
Section: 5.2
6)
Which of the following compounds will react most rapidly with HCl?
A)
Essential Organic Chemistry (Bruice)
Chapter 5
5-methyl-1-hexene
B)
4-methyl-1-hexene
C)
(E)-5-methyl-2-hexene
D)
(E)-2-methyl-3-hexene
E)
2-methyl-2-hexene
Answer:
E
Section: 5.2
7)
Answer:
Section: 5.3
8)
Answer:
Essential Organic Chemistry (Bruice)
Chapter 5
Section: 5.3
9)
Answer:
Section: 5.3
10)
Answer:
Section: 5.3
11)
Answer:
Section: 5.3
Essential Organic Chemistry (Bruice)
Chapter 5
12)
Answer:
Section: 5.3
13)
Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclohexane as the major organic
product.
Answer:
Section: 5.3
Essential Organic Chemistry (Bruice)
Chapter 5
14)
A)
I
B)
II
C)
III
D)
IV
E)
V
Answer:
C
Section: 5.4
15)
Answer:
Section: 5.4
16)
Answer:
Section: 5.4
Essential Organic Chemistry (Bruice)
Chapter 5
17)
Complete the following reaction and provide a detailed, step-by-step mechanism for the process.
Answer:
Section: 5.4
18)
2-methylpentane
B)
2-methyl-1-pentanol
C)
2-methyl-2-pentanol
D)
2-methyl-3-pentanol
E)
1-methoxypentane
Answer:
C
Section: 5.4
19)
Provide the structure of the major organic product of the following reaction.
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
Section: 5.4
20)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.5
Essential Organic Chemistry (Bruice)
Chapter 5
21)
Answer:
Section: 5.5
22)
1
B)
2
C)
3
D)
4
E)
6
Answer:
E
Section: 5.6
Essential Organic Chemistry (Bruice)
Chapter 5
23)
A)
5-Bromo-2-heptyne
B)
3-Bromo-5-heptyne
C)
2-Bromo-2-methyl-4-hexyne
D)
5-Bromo-5,5-dimethylhexyne
E)
5-Bromo-5-methyl-2-hexyne
Answer:
E
Section: 5.7
24)
Write structures and give IUPAC names for all alkynes with molecular formula C5H8.
Answer:
Section: 5.7
25)
Essential Organic Chemistry (Bruice)
Chapter 5
2,5,5-trimethyl-3-heptyne
Section: 5.7
26)
1-pentyne
Section: 5.7
27)
1-bromo-3-hexyne
Section: 5.7
28)
HCCH
Section: 5.7
29)
Section: 5.7
30)
Section: 5.7
31)
How many distinct terminal alkynes exist with a molecular formula of C5H8?
A)
1
B)
2
C)
3
D)
4
E)
5
Answer:
B
Section: 5.7
32)
Essential Organic Chemistry (Bruice)
Chapter 5
How many distinct internal alkynes exist with a molecular formula of C6H10?
A)
1
B)
2
C)
3
D)
4
E)
5
Answer:
C
Section: 5.7
33)
A)
Neohexyne
B)
Trimethylpropyne
C)
Trimethylacetylene
D)
tert-Butylacetylene
E)
Isopropylacetylene
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
D
Section: 5.7
34)
Answer:
6,6,6-trichloro-2-hexyne
Section: 5.7
35)
Which of the following is a correct statement about the carbon-carbon triple bond in an alkyne?
A)
composed of one sigma bond, one pi bond and one delta bond
Answer:
C
Section: 5.8
Essential Organic Chemistry (Bruice)
Chapter 5
36)
What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure?
A)
sp3, sp2
B)
sp2, sp2
C)
sp, sp
D)
sp2, sp
E)
sp, sp2
Answer:
D
Section: 5.8
37)
Answer:
B
Section: 5.8
38)
What two atomic orbitals or hybrid atomic orbitals overlap to form the carbon-carbon bond in ethyne?
A)
sp3sp3
B)
pp
C)
sp2sp2
D)
ss
E)
spsp
Answer:
E
Section: 5.8
39)
What are the hybridizations of the carbon atoms numbered 1 and 2 in the structure below?
1 2
H3C-CHCH-CC-H
A)
sp3, sp2
B)
sp2, sp2
C)
sp2, sp
D)
Essential Organic Chemistry (Bruice)
Chapter 5
sp, sp
Answer:
D
Section: 5.8
40)
relatively nonpolar
B)
D
Section: 5.9
41)
A and B
E)
A, B, and C
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
D
Section: 5.9
42)
Although you might expect 1-propyne to be more reactive than 1-propene in electrophilic addition reactions, the reverse
is true. Explain this using your knowledge of the mechanism of electrophilic additions to both alkynes and alkenes.
Answer:
When HCl is added to an alkene, a secondary carbocation intermediate is formed, When HCl is added to an
alkyne, a vinylic carbocation is formed as an intermediate, Alkynes are less stable than alkenes but vinylic
carbocations are less stable than secondary carbocations. Thus, alkenes are more reactive than alkynes since the difference
in stabilities between the carbocations is greater than the difference in stabilities between the alkene and alkyne.
Section: 5.10
43)
Which of the following statements correctly describes the general reactivity of alkynes?
A)
The bonds of alkynes are higher in energy than the bonds and are thus more
reactive.
C)
A
Section: 5.10
Essential Organic Chemistry (Bruice)
Chapter 5
44)
Describe the role of the alkyne in the reaction between an alkyne and a hydrogen halide.
Answer:
An alkyne is an electron-rich molecule because of its two bonds and thus an alkyne is a nucleophile. electrons from the
alkyne triple bond attack the electrophilic hydrogen of the hydrogen halide during the first step of the reaction between
an alkyne and a hydrogen halide.
Section: 5.10
Essential Organic Chemistry (Bruice)
Chapter 5
45)
HCl
CH3CCH
A)
B)
C)
CH3CHCHCl
D)
E)
Answer:
B
Section: 5.10
46)
Provide the structure of the major organic product(s) in the reaction below.
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
Section: 5.10
47)
In the addition of hydrogen bromide to alkynes, which of the following species is believed to be an intermediate?
A)
vinyl anion
B)
vinyl cation
C)
vinyl radical
D)
carbene
E)
B
Section: 5.10
48)
Which of the following compounds is the major product when 1-hexyne is treated with excess HBr?
A)
1,1-dibromohexane
B)
1,1-dibromohexene
Essential Organic Chemistry (Bruice)
Chapter 5
C)
1,2-dibromohexene
D)
1,2-dibromohexane
E)
2,2-dibromohexane
Answer:
E
Section: 5.10
49)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.10
50)
Provide the structure of the major organic product of the following reaction.
Answer:
Essential Organic Chemistry (Bruice)
Chapter 5
Section: 5.10
Essential Organic Chemistry (Bruice)
Chapter 5
51)
A)
B)
C)
D)
E)
Answer:
E
Section: 5.11
Essential Organic Chemistry (Bruice)
Chapter 5
52)
Which of the following is the final and major product of this reaction?
A)
I
B)
II
C)
III
D)
IV
E)
V
Answer:
A
Section: 5.11
53)
Provide the structure of the major organic product(s) in the reaction below.
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
Section: 5.11
54)
hydroboration/oxidation
B)
hydrogenation
D)
both A and B
E)
D
Section: 5.11
Essential Organic Chemistry (Bruice)
Chapter 5
55)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.11
56)
H2/HCl
B)
H2/H2SO4
C)
H2/Ni
D)
H2O/Ni
E)
H2O/H2SO4
Answer:
C
Section: 5.12
Essential Organic Chemistry (Bruice)
Chapter 5
57)
Upon hydrogenation, which of the following alkenes releases the least heat per mole?
A)
3,4-dimethyl-1-hexene
B)
(Z)-3,4-dimethyl-2-hexene
C)
(E)-3,4-dimethyl-2-hexene
D)
(Z)-3,4-dimethyl-3-hexene
E)
(E)-3,4-dimethyl-3-hexene
Answer:
E
Section: 5.12
58)
H2/Pt
B)
H2/Lindlar's catalyst
C)
Li/NH3
D)
Na/NH3
E)
H+/Zinc dust
Answer:
B
Essential Organic Chemistry (Bruice)
Chapter 5
Section: 5.12
Essential Organic Chemistry (Bruice)
Chapter 5
59)
A mixture of 1-heptyne, 2-heptyne, and 3-heptyne was hydrogenated in the presence of a platinum catalyst until
hydrogen uptake ceased. If one assumes that the hydrogenation went to completion, how many distinct seven-carbon
hydrocarbons were produced?
A)
1
B)
2
C)
3
D)
6
E)
8
Answer:
A
Section: 5.12
60)
Provide the structure of the major organic product(s) in the reaction below.
Answer:
Section: 5.12
61)
Provide the structure of the major organic product of the following reaction.
Essential Organic Chemistry (Bruice)
Chapter 5
Answer:
Section: 5.12
62)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.12
63)
A>E>C>D>B
B)
A>E>D>B>C
Essential Organic Chemistry (Bruice)
Chapter 5
C)
E>A>C>B>D
D)
A>C>E>D>B
E)
E>D>B>A>C
Answer:
A
Section: 5.13
64)
65)
Which hydrogens are more acidic, those of benzene or those of cyclohexane? Why?
Answer:
Benzene. The carbon hybridization of benzene is sp2 while that of cyclohexane is sp3. The more s character in benzene
causes its hydrogens to be more acidic than those of cyclohexane.
Section: 5.13
66)
The carbanion which results upon deprotonation of a terminal alkyne has the lone pair of electrons in an sp hybridized
Essential Organic Chemistry (Bruice)
Chapter 5
orbital. The greater % s character of this orbital gives the orbital a significantly lower energy.
Section: 5.13
67)
CH3Li
B)
CH3ONa
C)
NaOH
D)
both B and C
E)
D
Section: 5.13
68)
Among the compounds water, 1-butyne, 2-butyne, and ethane, which are stronger acids than ammonia?
A)
B
Section: 5.13
69)
What type of organic product results when 1-butyne is treated with 6M aqueous NaOH?
A)
a sodium acetylide
B)
an enol
C)
an alcohol
D)
an aldehyde
E)
E
Section: 5.13
70)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.13
Essential Organic Chemistry (Bruice)
Chapter 5
71)
Provide the structure of the major organic product(s) in the reaction below.
CH3CH2CH
2. PhCH2Br
Answer:
CH3CH2CCCH2Ph
Section: 5.14
72)
Provide the structure of the major organic product of the following reaction.
Answer:
Section: 5.14
73)
Answer:
Essential Organic Chemistry (Bruice)
Chapter 5
Section: 5.15
74)
Describe a sequence of reactions by which 3-heptyne can be straightforwardly prepared from acetylene.
Answer:
1) NaNH2
2) CH3CH2Br
3) NaNH2
4) CH3CH2CH2Br
Section: 5.15
75)
1) NaNH2
2) CH3CH2Br
3) HgSO4, H2O, H2SO4
Section: 5.15
76)
1) NaNH2
2) CH3CH2Br
3) NaNH2
4) CH3Br
5) H2, Lindlar's catalyst
Section: 5.15
Essential Organic Chemistry (Bruice)
Chapter 5
77)
A)
CH2CH2 + HCCH
B)
CH3CH2CCH
C)
HCCBr
D)
HCCCH2CH2Br
E)
CH3CCCH3
Answer:
B
Section: 5.15
78)
What is the structure of the monomer from which the following polymer is made?
A)
CH3CH3
B)
CH2CH2
C)
CH3CHCH2
D)
CH2CHCHCH2
Essential Organic Chemistry (Bruice)
Chapter 5
E)
CH3CHCHCH3
Answer:
E
Section: 5.16
Essential Organic Chemistry (Bruice)
Chapter 5
79)
What is the structure of the monomer from which the following polymer is made?
A)
I
B)
II
C)
III
D)
IV
E)
V
Answer:
B
Section: 5.16
80)
Which of the following addition polymers results from the reaction below?
nCF2CF2 ?
A)
Essential Organic Chemistry (Bruice)
Chapter 5
[CF-CF]n
B)
[CF3-CF3]n
C)
[-CF2-CHCHCF2-]n
D)
[-CF2-CF2-]n
E)
[-CF2CF2-]n
Answer:
D
Section: 5.16
81)
Which of the following species can best serve as a radical initiator for radical polymerization?
A)
ROH
B)
ROR
C)
ROOR
D)
RCOOR
E)
RCOOH
Answer:
C
Section: 5.16
Essential Organic Chemistry (Bruice)
Chapter 5
82)
Which of the following is the first chain propagating step in the radical polymerization of ethylene using a peroxide
initiator?
A)
B)
RO + CH2CH2 ROCH2CH2
C)
RO + CH2CH2 ROCHCH2 + H
D)
ROOR + CH2CH2 2 ROH + CHCH
E)
2RO + CH2CH2 2 ROH + CHCH
Answer:
B
Section: 5.16
83)
1. Initiation
2. Propagation
3. Termination
Section: 1.2
Essential Organic Chemistry (Bruice)
Chapter 5
84)
Show the mechanism for the formation of a segment of polystyrene containing two molecules of styrene and initiated by
hydrogen peroxide.
Answer:
Section: 5.16
85)
Provide a mechanism to show how H2CC(CH3)2 is polymerized using BF3 as the initiatior.
Answer:
Section: 5.16
Essential Organic Chemistry (Bruice)
Chapter 5