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ch09 Testbank PDF
ch09 Testbank PDF
3. The decrease in entropy (the S value is negative) observed for alkene addition
reactions results from:
A) the breaking of a π and bond.
B) the formation of two bonds.
C) the reaction being exothermic.
D) two molecules reacting to form a single molecule.
E) the temperature dependence of the S term.
Ans: D
6. For an addition reaction, why does free energy, G, become more positive with
increasing temperature?
A) The positive entropy dominates at high temperature.
B) The negative entropy dominates at high temperature.
C) The positive enthalpy dominates at high temperature.
D) The negative enthalpy dominates at high temperature.
E) The enthalpy and entropy cancel at high temperature.
Ans: B
7. For this question, the “entropy term” refers to “-TΔS”. Addition reactions are
generally favorable at low temperatures because:
A) the positive enthalpy term is larger than the negative entropy term.
B) the negative enthalpy term is larger than the positive entropy term.
C) the positive enthalpy term is smaller than the negative entropy term.
D) the negative enthalpy term is smaller than the positive entropy term.
E) the enthalpy and entropy terms are equal.
Ans: B
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: E
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
12. Which of the structures shown depicts the most stable carbocation intermediate
formed in the hydrohalogenation reaction shown?
A) I
B) II
C) III
D) IV
E) V
Ans: B
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: B
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: C
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: A
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
16. What is the expected major product for the following reaction?
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Anti-Markovnikov Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: C
18. Which of the alkenes shown below would produce a chirality center upon
Markovnikov hydrohalogenation?
A)
B)
C)
D)
E)
Ans: B
Topic: Stereochemistry of Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
A)
B)
C)
D)
E)
Ans: A
20. Which of the alkenes below would be expected to produce at least one chirality
center upon hydrohalogenation in the presence of peroxide?
A)
B)
C)
D)
E)
Ans: B
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Moderate
21. Which of the given reaction schemes would produce the molecule shown below?
A)
B)
C)
D) Both A and B
E) Both B and C
Ans: E
22. Which of the molecules below are enantiomers formed as products upon reaction of
HBr with 4-methylpent-1-ene?
A) I and II
B) II and III
C) III and IV
D) I and III
E) II and IV
Ans: E
Topic: Hydrohalogenation and Carbocation Rearrangements
Section: 9.3
Difficulty Level: Moderate
A) I
B) II
C) III
D) I and II
E) II and III
Ans: D
A) I
B) II
C) III
D) I and II
E) II and III
Ans: D
Topic: Hydrohalogenation and Carbocation Rearrangements
Section: 9.3
Difficulty Level: Moderate
25. The expected major product(s) of HCl addition to the alkene shown would be:
A) II
B) II and III
C) I and IV
D) V
E) All of the above are equally likely to form
Ans: A
26. The expected major product(s) of HBr addition to the alkene shown would be:
A)
B)
C)
D)
E)
Ans: A
Topic: Stereochemistry of Hydrohalogenation and Carbocation Rearrangements
Section: 9.3
Difficulty Level: Moderate
27. The reaction shown below would be expected to produce as major products which
of the following compounds?
A)
B)
C)
D)
E)
Ans: D
28. What is the IUPAC name of the expected major product formed upon reaction of
HCl with 3-methyl-1-butene?
A) 1-chloro-2-methylbutane
B) 1-chloro-3-methylbutane
C) 2-chloro-2-methylbutane
D) 2-chloro-3-methylbutane
E) 1-chloropentane
Ans: C
Topic: Hydrohalogenation and Carbocation Rearrangements
Section: 9.3
Difficulty Level: Hard
A)
B)
C)
D) A and B
E) A and C
Ans: C
30. Identify the expected product(s) for the reaction shown below:
A)
B)
C)
D)
E)
Ans: C
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Easy
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Easy
A) I
B) II
C) III
D) IV
E) V
Ans: C
A)
B)
C)
D)
E)
Ans: D
A) I and III
B) II
C) III and V
D) IV
E) I, III and V
Ans: D
36. What is the expected major product for the following reaction?
A)
B)
C)
D)
E)
Ans: A
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Medium
37. Which of the following compounds would react most rapidly with a dilute aqueous
solution of H2SO4?
A) I
B) II
C) III
D) IV
Ans: C
38. The three compounds below can form a carbocation under aqueous acidic
conditions. Which ones will form the same carbocation?
A) I and II
B) I and III
C) II and III
D) All three will form the same carbocation
Ans: D
39. What would be the optimal conditions to effect the following transformation?
A) Dilute H2SO4
B) Concentrated H2SO4
C) Dilute HBr
D) Concentrated HBr
Ans: B
40. What would be the optimal conditions to effect the following transformation?
41. Which of the following is the major product of the reaction shown?
A) I
B) II
C) III
D) IV
Ans: D
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Hard
42. Which of the following correctly describes the product(s) of the reaction below?
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Easy
44. What is the expected major product for the following reaction?
A)
B)
C)
D)
E)
Ans: B
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Easy
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Easy
46. What is the expected major product for the following reaction?
A)
B)
C)
D)
E)
Ans: C
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Easy
47. What is the expected major product for the following reaction?
A)
B)
C)
D)
E)
Ans: D
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Easy
48. What is the expected major product for the following reaction?
A)
B)
C)
D)
E)
Ans: B
Topic: Oxymercuration-Demercuration
Section: 9.5
Difficulty Level: Moderate
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
A) H2O/H+
B) H2O/Peroxide
C) OH–
D) BH3.THF
E) 1. BH3.THF, 2. HO–, H2O2, H2O
Ans: E
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
52. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E)
Ans: E
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
53. What is (are) the expected major product(s) for the following reaction sequence?
A) I
B) II
C) III
D) I and II
E) I and III
Ans: E
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Moderate
54. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E)
Ans: E
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Moderate
55. What is the expected major product for the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Moderate
56. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E)
Ans: B
Topic: Catalytic Hydrogenation
Section: 9.7
Difficulty Level: Easy
58. Provide the organic product(s) for the reaction shown below.
A)
B)
C)
D)
E)
Ans: B
61. Which of the following sets of reagents accomplishes the transformation shown
below?
A) H2/HCl
B) H2/H2SO4
C) H2/Ni
D) H2O/Ni
E) H2O/H2SO4
Ans: C
62. Which of the reagents below are expected to convert cyclopentene into
cyclopentane?
A) H2 and Ni
B) H2O
C) Heat
D) Zn, H3O+
E) Light
Ans: A
Topic: Catalytic Hydrogenation
Section: 9.7
Difficulty Level: Easy
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
64. How many moles of hydrogen (H2) are consumed in the catalytic reduction of 1
mole of 1,3-dibromocyclohexa-1,4-diene?
A) 12
B) 2
C) 3
D) 4
E) None of the above
Ans: B
65. How many moles of hydrogen (H2) are required to completely reduce 1 mole of cis-
2,3,3-trimethylhepta-1,5-diene?
A) 02
B) 1
C) 2
D) 3
E) 4
Ans: C
Topic: Catalytic Hydrogenation
Section: 9.7
Difficulty Level: Easy
66. Which of the catalysts listed are used in the homogenous catalytic hydrogenation of
alkenes?
I) Ni II) Pt III) Wilkinson’s catalyst
A) I
B) II
C) III
D) I and II
E) II and III
Ans: C
69. For the catalytic hydrogenation of alkenes, select from below those most likely to
function as a homogenous catalyst?
A) Wilkinson’s catalyst
B) Ni
C) Pd
D) Pt
E) Au
Ans: A
70. Which of the following will yield 2-methylpentane upon catalytic hydrogenation?
A) 2-methyl-1-pentene 2
B) 2-methyl-2-pentene
C) 4-methyl-2-pentene
D) 4-methyl-1-pentene
E) All of the above
Ans: E
72. Identify the major organic product generated from the reaction shown.
A) I
B) II
C) III
D) IV
Ans: B
Topic: Halogenation
Section: 9.8
Difficulty Level: Easy
73. Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2
dissolved in CCl4?
A) I
B) II
C) III
D) IV
E) V
Ans: B
Topic: Halogenation
Section: 9.8
Difficulty Level: Easy
74. What is the expected major product upon reaction of 1-pentene with Cl2?
A) 1-chloropentane
B) 2-chloropentane
C) 1,1-dichloropentane
D) 2,2-dichloropentane
E) 1,2-dichloropentane
Ans: E
76. The expected first intermediate formed during a halohydrin reaction is:
A) a halonium ion.
B) the most stable carbocation with OH on the adjacent carbon.
C) the most stable carbocation with X on the adjacent carbon.
D) a cyclic oxonium ion.
E) the most stable carbanion.
Ans: A
78. What is the expected major product for the following reaction?
A) I
B) II
C) III
D) IV
E) V
Ans: D
79. Which of the statements is most correct regarding the products expected from the
halogenation reaction shown below?
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: anti dihydroxylation
Section: 9.9
Difficulty Level: Moderate
81. For the reaction sequence below, identify the expected major products.
A)
B)
C)
D)
Ans: B
82. For the reaction sequence below, identify the expected major product(s).
A) I
B) II
C) III
D) I and III
E) II and III
Ans: D
Topic: anti dihydroxylation
Section: 9.9
Difficulty Level: Moderate
83. What are the major products for the following reaction sequence?
A) I and II
B) II and III
C) III and IV
D) I and III
E) II and IV
Ans: E
84. What is the major product for the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: D
85. For the following dihydroxylation reaction which of the following statements is
correct regarding the expected products?
A) (Z)-3-methylpent-2-ene
B) (E)-3-methylpent-2-ene
C) 2-methylpent-2-ene
D) 2,3-dimethylbut-2-ene
E) none of the above
Ans: A
Topic: syn Dihydroxylation
Section: 9.10
Difficulty Level: Easy
87. Identify the expected major organic product resulting from the following reaction
sequence.
A) I
B) II
C) III
D) IV
E) V
Ans: A
A) I
B) II
C) III
D) IV
E) V
Ans: A
Topic: syn Dihydroxylation
Section: 9.10
Difficulty Level: Easy
89. Identify the expected major organic product generated from the reaction sequence
shown.
A) I
B) II
C) III
D) IV
Ans: B
90. Which of the following alkene addition reactions occur(s) specifically in syn
fashion?
A) dihydroxylation using OsO4, H2O2
B) addition of H2
C) hydroboration
D) addition of HCl
E) A, B, and C
Ans: E
Topic: syn Dihydroxylation
Section: 9.10
Difficulty Level: Easy
91. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E) None of the above
Ans: A
92. Provide the expected major organic product of the reaction sequence shown.
A) I and II
B) IV and V
C) I only
D) II only
E) III only
Ans: E
Topic: Oxidative Cleavage
Section: 9.11
Difficulty Level: Easy
93. Which of the following reagents effectively cleaves both the sigma and pi bonds of
a carbon-carbon double bond?
A) Cl2/hυ
B)
C) H2SO4
D) cold KMnO4
E) 1. O3 2. DMS
Ans: E
94. How many carbonyl groups are generated upon treatment of the molecule below
with ozone, followed by zinc metal and water?
A) 1
B) 2
C) 3
D) 4
E) 8
Ans: E
Topic: Oxidative Cleavage
Section: 9.11
Difficulty Level: Moderate
95. Of the alkenes shown, which would produce the product shown below, upon
treatment with ozone, followed by zinc metal and water?
A) I
B) II
C) III
D) IV
E) V
Ans: B
96. What is the expected major product of the reaction sequence shown below?
A) I
B) II
C) III
D) IV
E) V
Ans: A
Topic: Oxidative Cleavage
Section: 9.11
Difficulty Level: Moderate
97. What are the expected major products from the reaction sequence shown below?
A) I
B) II
C) III
D) IV
E) V
Ans: A
Topic: Predicting Addition Products
Section: 9.12
Difficulty Level: Easy
98. Which of the following alkene addition reactions occur(s) specifically in an anti
fashion?
A) hydroboration-oxidation
B) addition of Br2
C) addition of H2
D) addition of H2O in dilute acid
E) both A and B
Ans: B
100. What is the expected major product for the following reaction sequence?
A)
B)
C)
D)
E)
Ans: A
101. Which reagents are most likely to accomplish the transformation shown below?
A) I
B) II
C) III
D) IV
Ans: C
Topic: Predicting Addition Products
Section: 9.12
Difficulty Level: Moderate
103. The expected product(s) resulting from addition of Br2 to (E)-3-hexene would be:
A) a meso dibromide.
B) a mixture of optically active enantiomeric dibromides.
C) a mixture of optically inactive enantiomeric dibromides.
D) (Z)-3,4-dibromo-3-hexene.
E) (E)-3,4-dibromo-3-hexene.
Ans: A
104. Which of the following alkenes will yield a meso dihalide when reacted with
Br2/CCl4 at room temperature?
A)
B)
C)
D)
E) Both B and D
Ans: B
Topic: Predicting Addition Products
Section: 9.12
Difficulty Level: Moderate
105. What is the expected major product resulting from the acid-catalyzed hydration of
2,5-dimethyl-2-hexene?
A)
B)
C)
D)
E)
Ans: B
106. What is the expected major product resulting from treatment of (E)-3-methyl-3-
hexene with Br2 in the presence of methanol, CH3OH?
A)
B)
C)
D)
E) All of the above are produced in equal amounts
Ans: B (+ enantiomer)
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Easy
108. For the reaction sequence shown, what is the expected major product?
A) I
B) II
C) III
D) IV
E) V
Ans: D
109. What is the expected major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Moderate
110. What is the expected major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: A
111. Which is the correct sequence of reaction steps necessary to complete the following
transformation?
112. What is the expected major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Moderate
113. What is the expected major product of the following reaction sequence?
A)
B)
C)
D)
E)
Ans: A
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Moderate
114. What is the expected major product of the following reaction sequence?
A)
B)
C)
D)
E)
Ans: C
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Moderate
115. What is the expected major product of the following reaction sequence?
A)
B)
C)
D)
E)
Ans: A
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Hard
116. What is the expected major product of the following reaction sequence?
A) I
B) II
C) III
D) IV
E) V
Ans: C
117. For the following reaction sequence, which molecule is expected as the major
product?
A)
B)
C)
D)
E)
Ans: A + its diastereomer
118. What is the expected major product of the following reaction sequence?
A)
B)
C)
D)
E)
Ans: E
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Hard
119. For the following reaction sequence, identify the expected major organic products
and provide their stereochemical relationship.
120. Most bonds are quite susceptible to reaction with ____________________, also
referred to as electron-seeking reagents.
Ans: electrophiles
Topic: Regioselectivity
Section: 9.3
Difficulty Level: Easy
121. The rule that correctly predicts the regiochemistry of most ionic additions to
alkenes is named after which chemist?
Ans: Markovnikov's Rule
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
122. For the following reaction sequence provide the expected major organic product(s).
Include all stereoisomers showing relevant stereochemistry.
Ans:
Topic: Hydrohalogenation
Section: 9.3
Difficulty Level: Easy
123. Provide the structure(s) of the expected major organic product(s) generated upon
completion of the following reaction scheme:
Ans:
Topic: Hydrohalogenation and Carbocation Rearrangements
Section: 9.3
Difficulty Level: Moderate
124. The reaction of HCl with 2-ethyl-1-pentene or HCl with 3-methyl-2-hexene results
in the identical major product of 3-chloro-3-methylhexane. Provide a mechanistic
scheme showing the reaction of each alkene with HCl, including the intermediate and
product. Provide a brief explanation how the different alkene reactants were transformed
into the same product.
Ans:
Electrophilic addition of a proton in the reaction between HCl and either of the
alkenes will result in formation of the most stable intermediate carbocation, which
is the same intermediate in both cases. Addition of Cl– to the tertiary carbocation
formed in either case results in the observed product. The reason for the identical
major product is a consequence of regioselective addition to the double bond
forming the same tertiary carbocation intermediate.
Ans:
126. Addition of HI to the alkene of the cyclobutane in the scheme below, results in a
significant yield of the product shown. What other product(s) might also be
obtained? Explain with a mechanism and brief discussion the observation of the
given product as well as others that may arise.
Ans:
Regioselective addition of the proton of HI generates a secondary
carbocation. Rearrangement to a more stable 3o carbocation can occur by
two alternative pathways (1 and 2). Pathway 1 results in relief of ring
strain by expansion to a more stable 5-membered ring, as well as
stabilization by conversion of the secondary carbocation to a tertiary
carbocation. The second pathway involving a methyl shift is less likely;
although the rearrangement produces a more substituted carbocation (2°
3°), ring strain is not relieved and becomes worse with incorporation of
an sp2 carbon (bond angle 120°) into the cyclobutane (bond angle 90°).
The third pathway occurs if addition of iodide to occurs before
carbocation rearrangement. The first pathway is most likely, resulting in
the observed major product.
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Easy
127. For the following reaction sequence provide the expected major organic product(s).
Include all stereoisomers showing relevant stereochemistry.
Ans:
128. For the following reaction sequence provide the expected major organic product(s).
Include all stereoisomers and clearly show relevant stereochemistry.
Ans:
129. Provide the structure(s) of the expected major organic product(s) generated upon
completion of the following reaction scheme:
Ans:
Topic: Acid-Catalyzed Hydration
Section: 9.4
Difficulty Level: Moderate
130. The transformation shown below generates an achiral product from a chiral starting
material. Provide the structure of the expected product and a mechanism
explaining the transformation. Briefly explain why the product formed is achiral.
Ans:
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
131. A reaction that could potentially yield two or more constitutional isomers, but as in
hydroboration-oxidation produces only one isomer, is said to be
_____________________.
Ans: regioselective
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
Topic: Hydroboration-Oxidation
Section: 9.6
Difficulty Level: Easy
133. Provide the structure(s) of the expected major organic product(s) generated upon
completion of the following reaction scheme:
Ans:
134. Provide the expected major organic product from the reaction shown below.
Provide a brief explanation of any regioselectivity the reaction is expected to
produce.
Ans:
The alcohol will be found at the tertiary carbon, being the more substituted
carbon. Initial formation of the bromonium ion will favor attack of the
water at the more substituted carbon which is more capable of stabilizing
the partial positive charge that develops in the transition state.
135. For the following transformation below, provide a detailed step-wise mechanism
showing the electron flow using the curved arrow formalism.
Ans:
136. For the following reaction draw out the expected major organic product(s). Include
regiochemical and/or stereochemical details as relevant, and provide a short
justification for the product(s) drawn.
Ans:
The reaction takes place with Markovnikov regioselectivity and anti
stereospecificity, giving a racemic mixture of the halohydrin as the major
product.
137. Draw Fischer projections of the major product of the reaction between
(Z)-2-methyl-3-hexene and aqueous Br2.
Ans:
The reaction takes place with anti stereospecificity. Since the alkene is
symmetrically substituted, Markovnikov rule is not applicable, and the
reaction is not regioselective. The product mixture would therefore consist
of 2 pairs of enantiomers, which are constitutional isomers of each other.
Topic: Oxidative Cleavage
Section: 9.11
Difficulty Level: Easy
138. Provide the structure(s) of the expected major organic product(s) generated upon
completion of the following reaction scheme:
Ans:
and
139. Predict the structure(s) of the expected major organic product(s) of the following
reaction. Include regiochemical and/or stereochemical details as needed.
Ans:
The reaction takes place with Markovnikov regioselectivity and anti
stereospecificity. As the product is chiral, the products are diastereomers.
140. Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-2-
methyl-3-hexene and cold, alkaline KMnO4.
Ans:
The reaction takes place with syn stereospecificity, giving a racemic
mixture of the diol product.
Topic: Predicting Reaction Products: syn Dihydroxylation
Section: 9.12
Difficulty Level: Moderate
141. Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-
methyl-3-hexene and catalytic OsO4 with NMO.
Ans:
The reaction takes place with syn stereospecificity, giving a racemic
mixture of the diol product.
142. Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-
methyl-3-hexene and MCPBA, followed by aqueous acid.
Ans:
The reaction takes place with anti stereospecificity, giving a racemic
mixture of the diol product.
Topic: Synthetic Strategies
Section: 9.14
Difficulty Level: Moderate
Ans:
144. Identify the structure(s) of the expected major organic product(s) of the following
reaction. Draw the products in the expected chair conformations and include
regiochemical and/or stereochemical details as needed.
Ans:
i. t-BuOK/t-BuOH, heat
ii. MCPBA/CH2Cl2
iii. H3O+
Ans:
Hofmann elimination occurs upon heating with the bulky potassium tert-
butoxide base, through an E2 elimination. Epoxidation with MCPBA is
stereospecific (syn), giving diastereomeric epoxides. Ring opening of the
epoxides under acidic conditions is regio- and stereospecific.
Topic: Synthetic Strategies
Section: 9.13
Difficulty Level: Hard
146. For the following transformation a) identify the starting material with correct
stereochemistry and b) provide a complete reaction mechanism, including
stereochemistry, to account for the product shown.
Ans:
147. Consider the information given below and identify the structure of the unknown
compound A, with a molecular formula of C8H14. Compound A reacts with
Br2/CCl4. Upon reaction of A with excess H2/Ni 1-ethyl-2-methylcyclopentane is
produced. Subjecting A to ozonolysis, the product shown below is produced as the
major organic product. Draw the correct structure of compound A, and provide a
brief and clear explanation relating the data provide with the structure selected.
A. 3
B. 4
C. 5
D. 6
Ans: B
Topic: Predicting Alkene Products + Spectroscopy
Section 9.12 + Spectroscopy
Difficulty: Medium
149. How many distinct resonances would appear in the (proton-decoupled) 13C
NMR spectrum for the product of the following reaction?
A. 4
B. 5
C. 6
D. 7
Ans: B