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Package Title: Solomons Test Bank
Course Title: Solomons 11e

Chapter Number: 13
Question type: Multiple choice
1) The allyl radical has how many bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A
Topic: Molecular Orbitals

Section: 13.2
Difficulty Level: Medium
2) The allyl radical has how many electrons in bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: B

Section: 13.2
3) The allyl radical has how many electrons in non-bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

Section: 13.2
4) The allyl radical has how many π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: C

Section: 13.2
5) The HOMO of the allylic radical has how many electrons in its ground state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: A

Section: 13.2
6) The LUMO of the allylic radical has how many electrons in its ground state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

Section: 13.2
7) The HOMO of the allylic cation has how many electrons in its ground state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B

Section: 13.2
8) The allyl cation has how many electrons in bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: B

Section: 13.3
9) The allyl cation has how many bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

Section: 13.3
10) The allyl cation has how many π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: C

Section: 13.3
11) 1,3-Pentadiene has how many bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B

Section: 13.6
12) 1,3-butadiene has how many bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B

Section: 13.6
13) 1,3-Pentadiene has how many antibonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B

Section: 13.7
14) 1,3-butadiene has how many electrons in its ground state bonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: D

Section: 13.6
15) 1,3-butadiene has how many electrons in its ground state antibonding π molecular orbitals?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

Section: 13.6
16) The HOMO of 1,3-pentadiene has how many electrons in its ground state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B

Section: 13.6
17) The LUMO of 1,3-pentadiene has how many electrons in its ground state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

Section: 13.6
18) The HOMO of 1,3-pentadiene has how many electrons in its excited state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: A

Section: 13.6
19) The LUMO of 1,3-pentadiene has how many electrons in its excited state?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

Section: 13.6
20) Which carbocation would be least stable?
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Stability (Alkenes, Cations, Radicals)

Section: 13.3
Difficulty Level: Easy
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.3
22) Which carbocation would be most stable?
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.3
a)
b)
c)
d)
e)
Answer: C

Section: 13.3
a)
b)
c)
d)
e)
Answer: D

Section: 13.3
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.3
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.3
27) Which of the following dienes would you expect to be the most stable?
a) CH3CH=CHCH=CHCH3
b) CH3CH=CHCH2CH=CH2
c) CH2=CHCH2CH2CH=CH2
d) CH2=CHCH(CH3)CH=CH2
e) CH3CH=C=CHCH2CH3
Answer: A

Section: 13.8
a) CH3CH2CH=CHCH2CH=CHCH3
b) CH3CH=CHCH=CHCH2CH3
c) CH2=CHCH2CH2CH2CH=CH2
d) CH2=CHCH=CHCH2CH2CH3
e) CH3CH2CH=C=CHCH2CH3
Answer: B

Section: 13.7
29) Which of the following compounds would be the most stable?
a) I
b) II
c) III
d) IV
e) They are all of equal stability.
Answer: A

Section: 13.7
30) Which diene would be least stable?
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.7
e) CH3CH=C(CH3)CH=CHCH2CH3
Answer: E

Section: 13.7
32) Which of the following dienes would you expect to be the least stable?
e) CH3CH=C(CH3)CH=CHCH2CH3
Answer: C

Section: 13.7
33) Considering both configurational and conformational factors, select the most stable form of
2,4-hexadiene.
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.7
34) Considering both configurational and conformational factors, select the least stable form of
2,4-hexadiene.
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 13.7
35) Which alkene would you expect to be most stable?
a) CH2=CHCH2CH2CH=CH2
b)
c)
d)
e)
Answer: E

Section: 13.7
36) Arrange these hexadienes in order of expected decreasing stability.
a) V > II > I > III > IV

b) III > IV > II > I > V
c) IV > III > II > V > I
d) IV > III > I > II > V
e) I > II > IV > III > V
Answer: D
Section: 13.7
37) Arrange these hexadienes in order of expected increasing stability.
a) V < II < I < III < IV

b) III < IV < II < I < V
c) IV < III < II < V < I
d) IV < III < I < II < V
e) I < II < IV < III < V
Answer: A

Section: 13.7
38) Arrange these carbocations in order of expected increasing stability.
a) V < II < I < IV < III

b) V<I<II<IV<III
c) IV <I< II <V< III
e) I < II < IV < III < V
Answer: B

Section: 13.3
39) Arrange these carbocations in order of expected increasing stability.
a) V < II < I < IV < III

b) V<I<II<IV<III
c) IV <I< II <V< III
e) II < III < IV < V < I
Answer: E

Section: 13.3
40) Which is not an example of resonance?
a) I
b) II
c) III
d) IV
e) None of these choices are examples of resonance.
Answer: C
Topic: Resonance
Section: 13.4
41) Which is not an example of resonance?
a) I
b) II
c) III
d) IV
e) None of these choices are examples of resonance.
Answer: C
Topic: Resonance
Section: 13.4
42) Which is not a proper resonance structure for 1,3-butadiene?

a) CH2=CH–CH=CH2
b)
c)
d)
e) All of these answer choices are correct.
Answer: B
Topic: Resonance
Section: 13.4
43) Which pair does not represent a pair of resonance structures?
a) I
b) II
c) III
d) IV
e) All of these choices represent pairs of resonance structures.
Answer: D
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: D
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: D
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: D
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: E
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: E
Topic: Resonance
Section: 13.4
a) I
b) II
c) III
d) IV
Answer: E
Topic: Resonance
Section: 13.4
50) Select the structure of the conjugated diene.
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Alkene Classification

Section: 13.5
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.5
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.6
53) Select the structure of the isolated diene.
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 13.5
54) Select the structure(s) of the conjugated diene(s).
a) I and II
b) II and III
c) III and IV
d) I, II and V
e) V
Answer: C

Section: 13.5
55) Which of the following dienes is a cumulated diene?

b) CH2=CHCH=CHCH2CH3
c) CH3CH=C=CHCH2CH3
d) CH3CH=CHCH=CHCH3
e) CH3CH=CHCH2CH=CH2
Answer: C

Section: 13.5
56) Which of the following dienes is a cumulated diene?
a) CH2=CHCH2CH2CH2CH=CH2
b) CH2=CHCH=CHCH2CH2CH3
c) CH3CH=C=CHCH2CH2CH3
d) CH3CH=CHCH=CHCH2CH3
e) CH3CH2CH=CHCH2CH=CH2
Answer: C

Section: 13.5
57) Select the structure(s) in which the multiple bonds are conjugated.
a) I and II
b) II and III
c) III and IV
d) I, II and V
e) V
Answer: B
Section: 13.5
58) Select the structure(s) in which the multiple bonds are conjugated.
a) I and IV
b) II and III
c) III and V
d) I, II and III
e) V
Answer: A

Section: 13.5
59) What is an IUPAC name for
a) 2,3-methylhept-2-en-4-yne
b) 1,1,3-trimethylhex-3-yn-1-ene
c) 1,1,3-trimethyl-3-hexyn-1-ene
d) 2,3-dimethyl-2-hepten-4-yne
e) 5,6-dimethyl-5-hepten-3-yne
Answer: D
Topic: Nomenclature
Section: 4.5, 4.6 and 13.5
60) A correct IUPAC name of the compound below is:
a) 1-Bromo-1-methyl-2,5-cyclohexadiene
b) 3-Bromo-3-methyl-1,4-cyclohexadiene
c) 6-Bromo-6-methyl-1,4-cyclohexadiene
d) 2-Bromo-2-methyl-1,3-cyclohexadiene
e) None of these choices.
Answer: B
Topic: Nomenclature
Section: 4.5, 4.6 and 13.5
61) The substituent R on the bicyclic compound shown is considered to be?
a) axial
b) equatorial
c) endo
d) exo
e) trans
Answer: D
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
a) axial
b) equatorial
c) endo
d) exo
e) trans
Answer: C
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.6

a) axial
b) equatorial
c) endo
d) exo
e) trans
Answer: D
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
a) axial
b) equatorial
c) endo
d) exo
e) trans
Answer: C
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
a) axial
b) equatorial
c) endo
d) exo
e) trans
Answer: D
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
a) axial
b) equatorial
c) Endo
d) Exo
e) Trans
Answer: C
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
67) What is an IUPAC name for this triene?
a) (2E,4Z,6e)–2,4,6–Nonatriene
b) (2Z,4E,6Z)–2,4,6–Nonatriene
c) (2E,4Z,6Z)–2,4,6–Nonatriene
d) (3Z,5Z,7e)–3,5,7–Nonatriene
e) (3Z,5E,7e)–3,5,7–Nonatriene
Answer: C
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
Difficulty Level: Hard
68) What is an IUPAC name for this triene?
a) (2E,4Z,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene
b) (2Z,4E,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene
c) (2E,4Z,6e)–2,3,6,7–tetramethyl-3,5,7–Nonatriene
d) (2E,4Z,6e)– 2,3,6,7–tetramethyl-3,5,7–Nonatriene
e) (2E,4E,6e)–3,4,7,8–tetramethyl-2,4,6–Nonatriene
Answer: E
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
69) Which compound would have the shortest carbon-carbon single bond?
a) CH3–CH3
b) CH2=CH–CH3
c) HC≡C–C≡CH
d) CH2=CH–C≡CH
e) CH2=CH–CH=CH2
Answer: C
Topic: Bond Lengths

Section: 13.6
70) Which compound would have the shortest carbon-carbon single bond?
a) CH≡C–CH=CH–CH2–CH3
b) CH2=CH–CH=CH–CH3
c) HC≡C–CH2–C≡C–CH3
d) CH2=CH–C≡C–CH2–CH3
e) CH3–C≡C–C≡C–CH3
Answer: E
Topic: Bond Lengths

Section: 13.6
71) Which carbon-carbon bond in the following compound would you expect to be shortest?
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Bond Lengths

Section: 13.6
72) Which carbon-carbon bond in the following compound would you expect to be longest?
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Bond Lengths

Section: 13.6
73) Which alkene would you expect to have the highest heat of hydrogenation?
a)
b)
c)
d)
e)
Answer: A
Topic: Heat of Hydrogenation

Section: 13.7
74) Which alkene would you expect to have the smallest heat of hydrogenation?
b)
c)
d)
e)
Answer: E

Section: 13.7
75) Which alkene would you expect to have the smallest heat of hydrogenation?
a)
b)
c)
d)
e)
Answer: E

Section: 13.7
76) Which alkene would you expect to have the lowest heat of hydrogenation?
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.7
77) Which alkene would you expect to have the highest heat of hydrogenation?
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 13.7
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.7
a) I
b) II
c) III
d) IV
e) V
Answer: B
Section: 13.7
80. Estimate the stabilization energy for 1,3-butadiene using the heats of hydrogenation
in Table 1.
Table 1.
Heats of Hydrogenation for Selected Compounds
C MΔ
o o H
ml (
p e k
o s J
u Hm
n 2 o
d l
-
1
)
1 1 -
- 1
B 2
u 7
t
e
n
e
1 1 -
- 1
P 2
e 6
n
t
e
n
e
1 2 -
, 2
3 3
- 9
B
u
t
a
d
i
e
n
e
t 2 -
r 2
a 2
n 6
s
-
1
,
3
-
P
e
n
t
a
d
i
e
n
e
a) 13 kJ mol-1
b) 15 kJ mol-1
c) 28 kJ mol-1
d) 239 kJ mol-1
e) 112 kJ mol-1
Answer: B

Section: 13.7
81. Estimate the stabilization energy for 1,3-pentadiene using the heats of hydrogenation
in Table 1.
Table 1.
C MΔ
o o H
ml (
p e k
o s J
u Hm
n 2 o
d l
-
1
)
1 1 -
- 1
B 2
u 7
t
e
n
e
1 1 -
- 1 1
P 2
e 6
n -
t 1
e 1
n 5
e
t
r
a
n
s
-
2
-
p
e
n
t
e
n
e
1 2 -
, 2
3 3
- 9
B
u
t
a
d
i
e
n
e
t 2 -
r 2
a 2
n 6
s
-
1
,
3
-
P
e
n
t
a
d
i
e
n
e
a) 13 kJ mol-1
b) 15 kJ mol-1
c) 28 kJ mol-1
d) 239 kJ mol-1
e) 112 kJ mol-1
Answer: B

Section: 13.7
82. Estimate the stabilization energy for 1,3-cyclohhexadiene using the heats of
hydrogenation in Table 1.
Table 1.
C MΔ
o o H
ml (
p e k
o s J
u Hm
n 2 o
d l
-
1
)
C1 -
y 1
c 2
l 0
o
h
e
x
e
n
e
1 2 -
, 2
4 4
- 0
C
y
c
l
o
h
e
x
a
d
i
e
n
e
1 2 -
, 2
3 3
- 2
C
y
c
l
o
h
e
x
a
d
i
e
n
e
1 2 -
, 2
5 5
- 3
H
e
x
a
d
i
e
n
e
a) 13 kJ mol-1
b) 21 kJ mol-1
c) 8 kJ mol-1
d) 120 kJ mol-1
e) 112 kJ mol-1
Answer: C

Section: 13.7
83) Which compound would have a UV absorption band at longest wavelength?
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: UV-Vis Spectroscopy
Section: 13.8
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.8
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.8
86) Select the most energetically favorable UV transition for 1,3-butadiene.
a) n ⎯⎯⎯→ σ*
b) n ⎯⎯⎯→ π*
c) π2 ⎯⎯⎯→ π3*
d) σ ⎯⎯⎯→ σ*
e) π1 ⎯⎯⎯→ π4*
Answer: C

Section: 13.8
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.8
88) Which of these symbols is used in connection with the intensity of absorption in the UV-
visible region?
a) ∝
b) ν
c) ε
d) λ
e) θ
Answer: C

Section: 13.8
89) Ignoring stereochemistry, the 1:1 reaction of bromine with 1,3-cyclohexadiene at 25°C in the
dark and in the absence of peroxide forms which of these?
a) I
b) II
c) III
d) IV
e) Both I and II
Answer: E
Topic: Conjugate Addition Reactions

Section: 13.9
90) Ignoring stereochemistry, the 1:1 reaction of chlorine with 1,3-cyclohexadiene at 25°C in the
dark and in the absence of peroxide forms which of these?
a) I
b) II
c) III
d) IV
e) Both I and II
Answer: E

Section: 13.9
91) Keeping in mind stereochemistry, how many products are formed by the reaction of one
equivalent of HBr with 2-methyl-1,3-cyclohexadiene?
a) 2
b) 4
c) 6
d) 8
e) 10
Answer: C

Section: 13.9
92) Which of the following dienes might react with bromine in CCl4 to yield 2,5-dibromo-3-
hexene?
b) CH2=CHCH=CHCH2CH3
c) CH3CH=C=CHCH2CH3
d) CH3CH=CHCH=CHCH3
e) CH3CH=CHCH2CH=CH2
Answer: D

Section: 13.9
93) Indicate which products would be obtained from the chlorination of 1,5-hexadiene at high
temperature (500°c), using a 1:1 mole ratio of the reactants.
a) I and II
b) II and III
c) III and IV
d) IV and V
e) V and I
Answer: C

Section: 13.9
94) Which reagent would convert 1,3-pentadiene into 3-penten-2-ol?
a) KMnO4/-OH
b) OsO4
c) H2O2, then H3O+

d) Cl2/H2O
e) H3O+
Answer: E
Topic: 1,2 Reactions of Conjugated Dienes

Section: 13.9
95) Which reagent would convert 1,3-octadiene into 3-octen-2-ol?
a) KMnO4/-OH
b) OsO4
c) H2O2, then H3O+

d) Cl2/H2O
+
e) H3O
Answer: E
Topic: 1,2 Reactions of Conjugated Dienes

Section: 13.9
96) Which is the only compound which can be completely ruled out as a product of the reaction
of 1,3-butadiene with HCl?
a) (S)-3-chloro-1-butene
b) (R)-3-chloro-1-butene
c) (e)-1-chloro-2-butene
d) (Z)-1-chloro-2-butene
e) (Z)-2-chloro-2-butene
Answer: E

Section: 13.9
97) How could the following synthesis be carried out?
a) (1) Br2/CCl4; (2) CH3CH2MgCl, ether; (3) CH3ONa/CH3OH

b) (1) HBr, 80°C; (2) (CH3CH2)2CuLi, ether
c) (1) HBr, 80°C; (2) Mg, ether; (3) CH3CH2OH, then H3O+
d) More than one of these choices.
e) All of these choices.
Answer: B
Topic: Multistep Synthesis

Section: 13.9
98) How could the following synthesis be carried out?
a) (1) Br2/CCl4; (2) CH3MgCl, ether; (3) CH3ONa/CH3OH

b) (1) HBr (1 eq); (2) (CH3)2CuLi, ether
c) (1) HBr (1eq); (2) Li, ether; (3) CuI; (4) CH3Br
d) More than one of these choices.
Answer: C
Topic: Multistep Reaction Synthesis

Section: 13.9
99) A thermodynamically-controlled reaction will yield predominantly:
a) the more/most stable product.

b) the product whose formation requires the smallest free energy of activation.
c) the product that can be formed in the fewest steps.
d) the product that is formed at the fastest rate.
e) the product which possesses the greatest potential energy.
Answer: A
Topic: Reaction Mechanisms and Control

Section: 13.9
100) An equilibrium-controlled reaction will yield predominantly:
a) the more/most stable product.

b) the product whose formation requires the smallest free energy of activation.
c) the product that can be formed in the fewest steps.
d) the product that is formed at the fastest rate.
e) the product which possesses the greatest potential energy.
Answer: A

Section: 13.9
101) A reaction under kinetic (or rate) control will yield predominantly:
a) the most stable product.

b) the product that can be formed in the fewest steps.
c) the product whose formation requires the smallest free energy of activation.
d) the product with the greatest potential energy.
e) the product with the least potential energy.
Answer: C

Section: 13.9
102) The accompanying diagram, which describes the fate of the intermediate in a reversible
reaction, implies that:
a) the less stable product forms more rapidly.

b) the more stable product forms more rapidly.
c) product B will predominate at equilibrium.
d) the intermediate has a short lifetime.
e) No conclusions can be drawn as to either reaction rate or product stability.
Answer: B

Section: 13.9
103) The accompanying diagram, which describes the fate of the intermediate in a reversible
reaction, implies that:
a) the less stable product forms more rapidly.

b) the more stable product forms more rapidly.
c) product B will predominate at equilibrium.
d) the intermediate has a short lifetime.
e) No conclusions can be drawn as to either reaction rate or product stability.
Answer: A

Section: 13.9
104) The accompanying diagram implies that:

a) the formation of B from A would be favored at high temperature.
b) the more stable product forms more rapidly from the intermediate species.
c) the formation of B from the intermediate is the rate-limiting step in the transformation of A
into B
d) the formation of B from A is not a concerted reaction.
e) All of these statements are true.
Answer: E

Section: 13.9
105) Which is an untrue statement concerning the Diels-Alder reaction?
a) The reaction is a syn addition.

b) The diene must be in the s-cis conformation to react.
c) Most Diels-Alder reactions are reversible.
d) Generally, the adduct formed most rapidly is the exo product.
e) Electron donating groups on the diene and electron withdrawing groups on the dieneophile
favor adduct formation.
Answer: D
Topic: Diels-Alder Reaction

Section: 13.10
106) Which of these dienes can undergo the Diels-Alder reaction?
a)
b)
c)
d)
e) All of these choices can undergo the Diels-Alder reaction.
Answer: A

Section: 13.10
a)
b)
c)
d)
e)
Answer: B

Section: 13.10
108) Which of the following can undergo the Diels Alder reaction?
a) I and II
b) II and III
c) III and IV
d) I, II and V
e) V
Answer: C

Section: 13.10
109) From the standpoint of reactivity, which is the poorest choice of dienophile to react with
2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?
a) I
b) II
c) III
d) IV
e) V
Answer: B
Section: 13.10
110) What is the product of the following reaction?
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.10
111) Which would be the best synthesis of the following compound?
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.10
112) Which reaction would produce the following compound?

a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: B

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: A

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: B

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
121) Which of the following pairs of compounds could be used as the basis for a Diels-Alder
synthesis of the compound shown below?
a) I
b) II
c) III
d) IV
e) More than one of these choices.
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.10
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.10
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 13.10
125) does not undergo the Diels-Alder reaction because:
a) ring systems cannot function as the diene component.

b) it cannot adopt the s-cis conformation.
c) it lacks electron-withdrawing groups.
d) it lacks strong electron-releasing groups.
e) the two double bonds are farther apart than in a non-cyclic conjugated system.
Answer: B

Section: 13.10
126) does not undergo the Diels-Alder reaction as a diene because:

Answer: A

Section: 13.10

Answer: B

Section: 13.10

Answer: B

Section: 13.10

e) the two double bonds are further apart than in a non-cyclic conjugated system.
Answer: B

Section: 13.10
130) Which of these dienes is the most reactive in the Diels-Alder reaction?
a)
b)
c)
d)
e)
Answer: C

Section: 13.10
131) Which of the following dieneophiles is most reactive in a Diels-Alder reaction:
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.10
132) Which of the following dieneophiles is most reactive in a Diels-Alder reaction:
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 13.10
133) Which diene and dienophile would you choose to synthesize the following compound?
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: B

Section: 13.10
135) Which diene would be least reactive toward Diels-Alder addition of maleic anhydride?
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 13.10
136) What would be the product of the following reaction?

a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: A

Section: 13.10
138) Which of the following would afford a synthesis of the following compound?
a) I
b) II
c) III
d) IV
Answer: D
Section: 13.10
139) What is the product of the following Diels-Alder cycloaddition reaction:
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
143) Which diene would you expect to react most rapidly with maleic anhydride?
a) I
b) II
c) III
d) IV
e) V
Answer: D
Section: 13.10
144) Which of these conjugated dienes can undergo a Diels-Alder reaction?
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.10
145) Which of these conjugated dienes can undergo a Diels-Alder reaction?
a) I
b) II
c) III
d) IV
Answer: E

Section: 13.10
146) Which of these dienes can undergo a Diels-Alder reaction?
a) I and V
b) I, II and V
c) III
d) IV
e) III and IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: B

Section: 13.10
a) I and VI
b) II and V
c) III and IV
d) IV and V
e) I and III
Answer: E

Section: 13.10
a) I and VI
b) II and V
c) III and IV
d) IV and V
e) I and III
Answer: A

Section: 13.10
151) Which compounds could be used in a Diels-Alder synthesis of
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: C

Section: 13.10
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: A

Section: 13.10
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: A

Section: 13.10

a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: A

Section: 13.10
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: E

Section: 13.10
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: E

Section: 13.10
a) I and III
b) I and IV
c) II and III
d) II and IV
e) I and II
Answer: E

Section: 13.10
158) Which is the major product of the following reaction?
a) I
b) II
c) III
d) IV
Answer: D

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: A

Section: 13.10
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 13.10
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 13.10

a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 13.10
a) I
b) II
c) III
d) IV
Answer: B

Section: 13.10
164) Which of these dienes is the most reactive in the Diels-Alder reaction?
a) 1,3-Butadiene
b) 1,4-Pentadiene
c) 2,3,-Dimethyl-1,3-butadiene
d) 1,2-Butadiene
e) 1,4-Cyclohexadiene
Answer: C

Section: 13.10
a) 1,3-Pentadiene
b) 1,4-Pentadiene
c) 1,2-Butadiene
d) 1,4-Cyclohexadiene
e) All of these choices can undergo the Diels-Alder reaction.
Answer: A

Section: 13.10
a) 1,2-Heptadiene
b) 1,3-Heptadiene
c) 1,4-Heptadiene
d) 1,5-Heptadiene
e) 1,6-Heptadiene
Answer: B

Section: 13.10
167) How would you synthesize:
a) I
b) II
c) III
d) IV
e) V
Answer: A
Section: 13.10
Question type: fill-in-the-blank
168) Systems that have a p orbital on an atom adjacent to a double bond are called ___ systems.
Answer: conjugated unsaturated
Topic: General
Section: 13.1
169) The hydrogen atom on a saturated (sp3) carbon adjacent to a double bond is called an ___
hydrogen.
Answer: allylic
Topic: General
Section: 13.1
170) The hydrogen atom on a carbon that is part of a double bond is called a ___ hydrogen.
Answer: vinyl or vinylic
Topic: General
Section: 13.1
171) Allylic radicals are ___ stable than tertiary radicals.
Answer: more
Topic: General
Section: 13.1
172) Vinyl cations are ___ stable than tertiary cations.
Answer: less
Topic: General
Section: 13.3
173) There are three types of polyenes (molecules containing two or more double bonds). They
are: ___.
Answer: conjugated, cumulated, isolated
Topic: General
Section: 13.5
174) Polyenes in which single and double bonds alternate along the carbon chain are called ___.
Answer: conjugated
Topic: General
Section: 13.5
175) UV-vis spectroscopy can be used to indicate whether ___ is present.
Answer: conjugation
Topic: General
Section: 13.8
176) When the product distribution for a particular reaction reflects the relative stabilities of the
products, the reaction is said to be under ___ control.
Answer: thermodynamic
Topic: General
Section: 13.9
177) When the product distribution for a particular reaction reflects the relative rate at which the
products are formed, the reaction is said to be under ___ control.
Answer: kinetic
Topic: General
Section: 13.9
178) A thermodynamically-controlled reaction will yield predominantly: ___.
Answer: the more/most stable product.
Topic: General
Section: 13.9
179) The Diels-Alder reaction is a cycloaddition between a conjugated ___ and a ___.
Answer: diene; dienophile
Topic: General
Section: 13.10
180) Stereochemically speaking, the Diels-Alder reaction is ___ and occurs with ___ of the
dienophile stereochemistry.
Answer: stereospecific; retention
Topic: General
Section: 13.10
181) A reaction under kinetic (or rate) control will yield predominantly: ___.
Answer: the product whose formation requires the smallest free energy of activation.
Topic: General
Section: 13.9
182) Conjugated dienes routinely undergo 1,2 and 1,4 addition reactions with a variety of
electrophilic reagents; this suggests that ___ are likely intermediates during these reactions.
Answer: allylic carbocations
Topic: General
Section: 13.9
Question type: Molecular drawing
183) Draw the structural formula for (R)-5-bromo-2,5-dimethyl-1,3-cyclopentadiene, clearly

indicating stereochemical details.
Answer:
Topic: Nomenclature
Section: 4.5, 4.6, 5.7, and 13.5
184) Draw the structural formula for (2E,4Z,6e)–3,4,7,8–tetramethyl-2,4,6–nonatriene, clearly

Answer:
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
185) Draw the structural formula for (2Z,4Z,6Z)-3,4,8-trimethyl-2,4,6-nonatriene, clearly

Answer:
Topic: Nomenclature
Section: 4.5, 4.6, 7.2 and 13.5
186) Predict the product(s) of the following reaction:
Answer:
Topic Conjugate Addition

Section: 13.9
Question type: fill-in-the-blank
187. During Diels-Alder reactions, when two stereoisomer products, exo and endo, are possible,
the ___ product is typically obtained as the major product.
Answer: endo
Topic: Diels-Alder Reactions

Section: 13.10
Question type: Essay
188) What reagents would be needed to synthesize the following substance via the Diels-Alder
reaction? Give stereochemical details, as relevant.
Answer:

Section: 13.10
189) Which diene and dienophile would you use to prepare the following molecule using a Diels-
Alder cycloaddition reaction:
Answer:

Section: 13.10
Answer:

Section: 13.10
191) The first step in the total synthesis of synthetic cholesterol involves production of the
intermediate structure shown. Which combination of diene and dieneophile will result in its
preparation?
Answer:

Section: 13.10
192) The structure below is an intermediate along the way to the production of synthetic
morphine. It is produced through a Diels-Alder cycloaddition reaction. Which combination of
diene and dieneophile will result in its preparation?
Answer:

Section: 13.10
193) What combination of diene and dieneophile can be used to prepare the following compound
through a Diels-Alder cycloaddition reaction:
Answer:

Section: 13.10
194) Predict the product of the following Diels-Alder cycloaddition reaction:
Answer:
Topic Diels-Alder Reaction

Section: 13.10
195) Steroids are naturally occurring polycyclic compounds classified as lipids. The Diels-Alder
reaction has been widely used in their preparation. Shown below is a precursor molecule used in
a total steroid synthesis. What combination of diene and dieneophile can be used to prepare this
compound through the use of a Diels-Alder cycloaddition reaction.
Answer:
Topic Diels-Alder Reaction

Section: 13.10
196) Draw arrows to indicate the electron flow for the following intramolecular Diels-Alder
cycloaddition reaction:
Answer:
Topic: Diels-Alder Mechanism

Section: 13.10
197) Draw arrows to indicate electron movement that explains the formation of the products
shown for the following retro-Diels-Alder reaction:
Answer:
Topic: Diels-Alder Mechanism

Section: 13.10
198) The compound shown below undergoes a retro-Diels-Alder cycloaddition reaction to yield
carbon dioxide and another compound. Predict the structure of the other compound formed.
Answer:

Section: 13.10
199) The alkaloid colchicine is used in the treatment of gout. The first synthetic colchine
involved the preparation of the key intermediate shown. Which combination of diene and
dieneophile will result in its preparation?
Answer:

Section: 13.10
Answer:

Section: 13.10
201) Complete the following sequence of reactions, giving structural details of all key
intermediates.
Answer:
Topic: Multistep Reactions

Section: 13.10
intermediates.
Answer:

Section: 13.10
intermediates.
Answer:

Section: 13.2, 13.10
204) Show the steps and reagents necessary to prepare the following compound. Use
retrosynthetic analysis as a tool to guide your synthesis.
Answer:
Topic: Multistep Reactions/Retrosynthetic Analysis

Section: 13.10
Answer:

Section: 13.10
Answer:
Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10
Answer:

Section: 13.10

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Package Title: Solomons Test Bank

Course Title: Solomons 11e

Question type: Multiple choice

1) The allyl radical has how many bonding π molecular orbitals?

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

4) The allyl radical has how many π molecular orbitals?

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

9) The allyl cation has how many bonding π molecular orbitals?

Topic: Molecular Orbitals

10) The allyl cation has how many π molecular orbitals?

Topic: Molecular Orbitals

11) 1,3-Pentadiene has how many bonding π molecular orbitals?

Topic: Molecular Orbitals

12) 1,3-butadiene has how many bonding π molecular orbitals?

Topic: Molecular Orbitals

13) 1,3-Pentadiene has how many antibonding π molecular orbitals?

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

Topic: Molecular Orbitals

20) Which carbocation would be least stable?

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

22) Which carbocation would be most stable?

Topic: Stability (Alkenes, Cations, Radicals)

23) Which carbocation would be most stable?

Topic: Stability (Alkenes, Cations, Radicals)

24) Which carbocation would be least stable?

Topic: Stability (Alkenes, Cations, Radicals)

25) Which carbocation would be most stable?

Topic: Stability (Alkenes, Cations, Radicals)

26) Which carbocation would be most stable?

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

30) Which diene would be least stable?

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

Topic: Stability (Alkenes, Cations, Radicals)

35) Which alkene would you expect to be most stable?

Topic: Stability (Alkenes, Cations, Radicals)

36) Arrange these hexadienes in order of expected decreasing stability.

a) V > II > I > III > IV

37) Arrange these hexadienes in order of expected increasing stability.

a) V < II < I < III < IV

Topic: Stability (Alkenes, Cations, Radicals)