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Klein, Organic Chemistry 3e
Chapter 8
1. In an addition reaction to an alkene, the π bond is ______.
A. a nucleophile
B. an electrophile
C. a leaving group
D. A and B
E. B and C
Answer: A
Learning Objective: 8.1 Define an addition reaction, name five kinds of addition
reactions, and list the groups added in each kind of reaction
Difficulty: Easy
2. Addition reactions of alkenes are characterized by _________.
A. formation of a π bond
B. addition of two groups across a double bond
C. breaking of a π bond
D. A and B
E. B and C
Answer: E
Learning Objective: 8.1 Define an addition reaction, name five kinds of addition
reactions, and list the groups added in each kind of reaction
Difficulty: Moderate
3. Alkenes are found in ________, which are used by living organisms to trigger
specific behavioral responses in other members of the same species.
Answer: pheromones
Learning Objective: 8.2 Provide examples of alkenes in both nature and industry
Difficulty: Easy
4. What is a compound that does not have a double bond?
A. allicin (garlic)
B. geraniol (roses)
C. cholesterol
D. limonene (oranges)
E. ammonia
Answer: E
Difficulty: Easy
5. Identify the compound that does not come from an alkene.
A. acetic acid
B. methanol
C. isopropyl alcohol
D. acetone
E. ethylene glycol
Answer: B
Difficulty: Easy
6. The alkene precursor to ethanol is __________.
Answer: ethylene or ethene

Difficulty: Easy
7. The alkene precursor to acetone is __________.
Answer: propylene or propene

Difficulty: Easy
8. Most π bonds are quite prone to reaction with an ____________________, also

referred to as electron-seeking reagents.
Answer: electrophile
Learning Objective: 8.3 Describe the role of temperature in determining whether an
addition or elimination reaction will occur and whether the reactants or products will be
favored
Difficulty: Easy
9. 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.
Answer: D
favored
Difficulty: Easy
10. Which statement best describes the temperature dependence of an addition

reaction?
A. Addition reactions are thermodynamically favored at all temperatures.

B. Addition reactions are thermodynamically disfavored at all temperatures.
C. Addition reactions are thermodynamically favored at low temperatures.
D. Addition reactions are thermodynamically favored at high temperatures.
E. Addition reactions are thermodynamically impossible.
Answer: C
favored
Difficulty: Easy
11. 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.
Answer: B
favored
12. 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
Answer: B
favored
Difficulty: Hard
13. The rule that correctly predicts the regiochemistry of most ionic additions to
alkenes is named after which chemist?
Answer: Vladimir Markovnikov

Learning Objective: 8.4 Define hydrohalogenation, describing the reaction in terms of its
regiochemistry and the effects of peroxides
Difficulty: Easy
14. Describe the regioselectivity and stereospecificity in the hydrohalogenation of an

alkene.
A. Markovnikov orientation with syn-addition

B. Markovnikov orientation with anti-addition
C. anti-Markovnikov orientation with syn-addition
D. anti-Markovnikov orientation with anti-addition
E. Markovnikov orientation with both syn- and anti-addition
Answer: E
Difficulty: Easy
15. In the addition reaction of HI to 2-methyl-2-butene, what is the first step?
A. attack of 2-methyl-2-butene initiated by an iodide ion

B. attack of 2-methyl-2-butene initiated by an iodine atom
C. isomerization of 2-iodo-2-methylbutene
D. formation of a carbocation at carbon two (C-2)
E. formation of carbocation at carbon three (C-3)
Answer: D
Difficulty: Easy
16. 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
Answer: B
17. Which of the molecules below would be the expected product for the
hydrohalogenation of the following alkene with HBr?
A. I
B. II
C. III
D. IV
E. V
Answer: E
Difficulty: Easy
18. What is the expected Markovnikov addition product from the addition of HI to 2-
methyl-2-butene?
A. 2-iodopentane
B. 2-iodo-2-methylbutane
C. 1-iodo-2-methylbutane
D. 1-iodo-3-methylbutane
E. 2-iodo-3-methylbutane
Answer: B
Difficulty: Easy
19. What compound is the expected product upon Markovnikov hydrohalogenation

with HBr of the alkene shown below?
A. I
B. II
C. III
D. IV
E. V
Answer: B
20. What is the expected major product of the following reaction?
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Easy
21. What is the expected major product of the following reaction?

A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Easy
22. What is the expected major product for the following reaction?
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
23. Which of the molecules below arises from the anti-Markovnikov hydrohalogenation
with HBr of the alkene shown?
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Easy
24. Which of the alkenes shown below would produce a chirality center upon
Markovnikov hydrohalogenation?
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Easy
25. What is the major product for the following reaction?
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Easy
26. Which of the alkenes below would be expected to produce at least one chirality
center upon hydrohalogenation in the presence of peroxide?
A. I
B. II
C. III
D. IV
E. V
Answer: B
27. Which of the given reaction schemes would produce the molecule shown below?
A. I
B. II
C. III
D. Both I and II
E. Both II and III
Answer: E
28. 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
Answer: E
29. Which of the following carbocations is (are) likely to undergo rearrangement
through a methyl shift?
A. I
B. II
C. III
D. I and II
E. II and III
Answer: D
30. Which of the following carbocations is (are) likely to undergo rearrangement

through a hydride shift?
A. I
B. II
C. III
D. I and II
E. II and III
Answer: D
31. What is the expected major product(s) of HCl addition to the alkene below?
A. II
B. II and III
C. I and IV
D. V
E. I and II
Answer: E
32. What are the expected major product(s) of HBr addition to the alkene shown
below?
A. I
B. II
C. III
D. IV
E. V
Answer: A
33. What is the major product of the reaction below?
A. I
B. II
C. III
D. IV
E. V
Answer: D
34. 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
Answer: C
Difficulty: Hard
35. Select the expected major product(s) of the following reaction.
A. I
B. II
C. III
D. I and II
E. I and III
Answer: C
Difficulty: Hard
36. Identify the expected product(s) for the reaction shown below.
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Hard
37. For the following reaction sequence provide the expected major organic
product(s). Include all stereoisomers showing relevant stereochemistry.
Answer:
Difficulty: Easy
38. Provide the structure(s) of the expected major organic product(s) generated upon
completion of the following reaction scheme:
Answer:
Difficulty: Easy
39. 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
explanation showing the reaction of each alkene with HCl, including the
intermediate and product. Provide a brief explanation of how the different alkene
reactants could be transformed into the same product.
Answer:
Electrophilic addition of a proton in the reaction between HCl and either of the alkenes
will result in the 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.
Difficulty: Hard
40. When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-

butene, are reacted with HCl the same major product is formed. Provide an
explanation for the observation.
Answer:
For the unsymmetrical 3,3-dimethyl-1-butene, the carbocation formed is 2°, but it can
readily undergo a methyl shift to form the more stable 3° carbocation, which is the same
as that formed from 2,3-dimethyl-2-butene. The addition of the chloride ion to the
carbocation forms the identical product, 2-chloro-2,3-dimethylbutane.
Difficulty: Hard
41. Addition of HI to the alkene 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.
Answer:
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.
Difficulty: Hard
42. Identify the description of the regioselectivity and stereospecificity in the acid-
catalyzed hydration of an alkene.

Answer: E
Learning Objective: 8.5 Describe an acid-catalyzed hydration reaction including
reactants, intermediates, products, regiochemistry, and stereochemistry
Difficulty: Easy
43. Give the expected major product of the following reaction.
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
44. Identify the expected major product of the following reaction.

A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Easy
45. Identify the expected major product of the following reaction.
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
46. Identify the major product from the treatment of 1-methylcyclohexene with H3O+.
A. I and III
B. II
C. III and V
D. IV
E. I, III and V
Answer: D
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Hard
48. Identify the compound that would react most rapidly with a dilute aqueous solution
of H2SO4.
A. I
B. II
C. III
D. IV
Answer: C
Difficulty: Medium
49. 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
Answer: D
Difficulty: Medium
50. What would be the optimal conditions to effect the following synthesis?
A. dilute H2SO4
B. concentrated H2SO4
C. dilute HBr
D. concentrated HBr
Answer: B
Difficulty: Medium
51. What would be the optimal conditions to effect the following synthesis?
A. dilute aqueous H2SO4

B. concentrated H2SO4
C. dilute aqueous HBr
D. concentrated HBr
Answer: A
Difficulty: Medium
52. Which of the following is the major product of the reaction shown?
A. I
B. II
C. III
D. IV
Answer: D
Difficulty: Hard
53. Describe the products of the reaction below.
A. only one stereoisomer

B. an equal mixture of enantiomers
C. a roughly equal mixture of diasteromers
D. a roughly equal mixture of constitutional isomers
Answer: B
Difficulty: Hard
product(s). Include all stereoisomers showing relevant stereochemistry.
Answer:

Difficulty: Easy
product(s). Include all stereoisomers and clearly show relevant stereochemistry.
Answer:

Difficulty: Easy
completion of the following reaction scheme.
Answer:

Difficulty: Easy
57. The synthesis shown below generates an achiral product from a chiral starting
material. Provide the structure of the expected product and a mechanism
explaining the synthesis. Briefly explain why the product formed is achiral.
Answer:
Upon addition of the proton to the alkene a 2° carbocation is formed that undergoes a
hydride shift to form a more stable 3° carbocation. The 3° carbocation is located in the
center of the chain. Addition of water to the central carbon produces a product with no
stereocenter and is thus achiral.

58. Give the best description of the regioselectivity and stereospecificity in the
oxymercuration of an alkene.

Answer: B
Learning Objective: 8.6 Discuss hydration of an alkene by oxymercuration-
demercuration, explaining why there is no carbocation rearrangement
Difficulty: Easy
59. What synthetic goal is achieved by subjecting an alkene to an oxymercuration-

demercuration reaction sequence?
A. Markovnikov addition of H2O, promoting skeletal rearrangement

B. Markovnikov addition of H2O, preventing skeletal rearrangement
C. anti-Markovnikov addition of H2O, promoting skeletal rearrangement
D. anti-Markovnikov addition of H2O, preventing skeletal rearrangement
E. anti-Markovnikov addition of H2O, syn-hydroxylation
Answer: B
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Easy
64. When an alkene is subjected to treatment with Hg(OAc)2 in alcohol, followed by

reaction with NaBH4, what functional group is formed?
A. ether
B. epoxide
C. alkane
D. syn diol
E. alkyne
Answer: A
65. A reaction that could potentially yield two or more constitutional isomers, but as in
hydroboration-oxidation produces only one isomer, is said to be
_____________________.
Answer: regioselective
Learning Objective: 8.7 Discuss the anti-Markovnikov addition of water across an
alkene by hydroboration-oxidation
Difficulty: Easy
66. Any proper mechanism of hydroboration-oxidation must explain the observed

_________ addition of the H and OH to the alkene as well as the _____________
regiochemistry.
Answer: syn, anti-Markovnikov

Difficulty: Easy
67. Give the best description for the regioselectivity and stereospecificity in the
hydroboration-oxidation of an alkene.

C. Anti-Markovnikov orientation with syn-addition
D. Anti-Markovnikov orientation with anti-addition
Answer: C
Difficulty: Easy
68. What reagents are needed to accomplish the following synthesis?
A. H2O/H+
B. H2O/Peroxide
C. OH–
D. BH3.THF
E. 1. BH3.THF; 2. HO–, H2O2, H2O
Answer: E
Difficulty: Easy
69. What is the expected major product for the following reaction sequence?
A. I
B. II
C. III
D. IV
E. V
Answer: E
Difficulty: Easy
70. 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
Answer: E
A. I
B. II
C. III
D. IV
E. V
Answer: E
A. I
B. II
C. III
D. IV
E. V
Answer: D
A. I
B. II
C. III
D. IV
E. V
Answer: B
completion of the following reaction scheme.
Answer:

Difficulty: Easy
75. Identify the product from the hydrogenation of an alkene.
A. dihaloalkane
B. alkane
C. haloalkane
D. alcohol
E. ether
Answer: B
Learning Objective: 8.8 Explain why catalytic hydrogenation proceeds via syn addition
Difficulty: Easy
76. Provide the organic product(s) for the reaction shown below.
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Easy
77. What is the name of the product formed when 5-chloro-1-methylcyclohexene is

reduced with a Pt catalyst and H2?
A. 1-chloro-2-methylcyclohexane
B. 1-chloro-3-methylcyclohexane
C. 1-chloro-5-methylcyclohexane
D. 3-chloro-1-methylcyclohexane
E. None of the above
Answer: B
Difficulty: Easy
78. What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C

and H2?
A. No reaction
B. cis-1,2-dimethylcyclohexane
C. trans-3,4-dimethylhexane
D. trans-1,2-dimethylhexane
Answer: A
Difficulty: Easy
79. Which of the following sets of reagents accomplishes the synthesis shown below?
A. H2/HCl
B. H2/H2SO4
C. H2/Ni
D. H2O/Ni
E. H2O/H2SO4
Answer: C
80. 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
Answer: A
Difficulty: Easy
81. Which alkene would yield 3-methylpentane upon subjection to catalytic

hydrogenation?
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Easy
82. How many moles of hydrogen (H2) are consumed in the catalytic reduction of 1
mole of 1,3-dibromocyclohexa-1,4-diene?
A. 1
B. 2
C. 3
D. 4
Answer: B
Difficulty: Easy
83. How many moles of hydrogen are required to completely reduce 1 mole of cis-
2,3,3-trimethylhepta-1,5-diene?
A. 0
B. 1
C. 2
D. 3
E. 4
Answer: C
Difficulty: Easy
84. 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
Answer: C
Difficulty: Easy
85. In conducting the catalytic hydrogenation of an alkene, which catalyst listed is

most likely soluble in the reaction medium?
A. Ni
B. Pt
C. Pd
D. Wilkinson’s catalyst
E. All of the above are soluble
Answer: D
Difficulty: Easy
86. Wilkinson’s catalyst accomplishes which of the listed molecular syntheses?
A. syn addition of H2 to an alkene

B. anti addition of H2 to an alkene
C. syn dihydroxylation of an alkene
D. anti dihydroxylation of an alkene
E. oxidative cleavage of an alkene
Answer: A
Difficulty: Easy
87. Identify Wilkinson’s catalyst.
A. (Ph3P)3RhCl
B. (Ph3P)3RhBr
C. (Ph3P)3PbCl
D. (Ph3P)3PbBrl
E. (Ph3P)3RuCl
Answer: A
Difficulty: Easy
88. Which of the following will yield 2-methylpentane upon catalytic hydrogenation?
A. 2-methyl-1-pentene
B. 2-methyl-2-pentene
C. 4-methyl-2-pentene
D. 4-methyl-1-pentene
E. All of the above
Answer: E
89. For the complete reduction of 1 mole of 3E,5E.-hepta-1,3,5-triene with H2 using a

Pd catalyst, how many moles of H2 are consumed?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: C
90. Identify the major organic product generated from the reaction shown.
A. I
B. II
C. III
D. IV
Answer: B
91. Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2
dissolved in CCl4?
A. I
B. II
C. III
D. IV
E. V
Answer: B
Learning Objective: 8.9 Describe a halogenation reaction, including reactants,
intermediates, products, and stereochemistry
Difficulty: Easy
92. 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
Answer: E
Difficulty: Easy
93. Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following
as the major product?
A. 2,3-dibromo-2-methylpentane
B. 2,2-dibromo-3-methylpentane
C. 3,3-dibromo-2-methylpentane
D. 2-bromo-2-methylpentane
E. 3-bromo-2-methylpentane
Answer: A
Difficulty: Easy
94. Which of the statements is most correct regarding the products expected from the
halogenation reaction shown below?
A. Equal amounts of I and II are produced.

B. Equal amounts of III and IV are produced.
C. Equal amounts of I and IV are produced.
D. Equal amounts of II and III are produced.
E. Equal amounts of I and III are produced.
Answer: A
Difficulty: Hard
95. Identify the expected first intermediate formed during a halohydrin reaction.
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.
Answer: A
Difficulty: Easy
96. What major product is expected from the following reaction?
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Easy
98. 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.
Answer:
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity.
The starting material is shown as a single enantiomer, and thus produces two
diastereomers. The product containing the cis fused rings is capable of a ring flip.

Difficulty: Hard
99. The reaction of Br2 with 1-methylcyclohexene, in the presence of ethylamine

(EtNH2), is expected to produce which of the following as the major product?
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Hard
100. Provide the expected major organic product from the reaction shown below.
Provide a brief explanation of any regioselectivity the reaction is expected to
produce.
Answer:
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.

Difficulty: Easy
101. For the following equation, provide a detailed step-wise mechanism showing the
electron flow using the curved arrow formalism.
Answer:

Difficulty: Hard
102. 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.
Answer:
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity,
giving a racemic mixture of the halohydrin as the major product.
103. Draw Fischer projections of the major product of the reaction between
(Z)-2-methyl-3-hexene and aqueous Br2.
Answer:
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.

104. For the reaction sequence below, identify the expected major products.
A. I
B. II
C. III
D. IV
Answer: B
Learning Objective: 8.10 Describe the process for anti dihydroxylation
105. 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
Answer: D
106. 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
Answer: E
107. What is the major product for the following reaction sequence?
A. I
B. II
C. III
D. IV
E. V
Answer: D
108. For the following dihydroxylation reaction which of the following statements is
correct regarding the expected products?
A. Equal amounts of I and II produced
B. Equal amounts of III and IV produced
C. Equal amounts of I and IV produced
D. Equal amounts of II and III produced
E. Equal amounts of I and III produced
Answer: E
Difficulty: Hard
109. An unknown alkene was reacted with MCPBA in dichloromethane, followed by

work-up with H2O/H+. A racemic mixture of the compound shown below was
obtained. What is correct name of the starting alkene?
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
Answer: A
Difficulty: Hard
110. Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-
methyl-3-hexene and MCPBA, followed by aqueous acid.
Answer:
The reaction takes place with anti stereospecificity, giving a racemic mixture of the diol
product.

111. Identify the expected major organic product resulting from the following reaction
sequence.
A. I
B. II
C. III
D. IV
E. V
Answer: A
Learning Objective: 8.11 Describe a syn dihydroxylation reaction
112. Treatment of 1,2-dimethylcyclopentene with OsO4, followed by aqueous NaHSO3,

produces which of the following?
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Easy
113. Identify the expected major organic product generated from the reaction sequence
shown.
A. I
B. II
C. III
D. IV
Answer: B
Difficulty: Easy
114. Which of the following alkene addition reactions occur(s) specifically in syn
fashion?
A. dihydroxylation using OsO4, H2O2

B. addition of H2
C. hydroboration, oxidation
D. addition of HCl
E. A, B, and C
Answer: E
Difficulty: Easy
A. I
B. II
C. III
D. IV
Answer: A
Difficulty: Easy
116. 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
Answer: E
Learning Objective: 8.12 Describe the formation of carbonyl groups by ozonolysis
Difficulty: Easy
117. Which of the following reagents effectively cleaves both the sigma and pi bonds of
a carbon-carbon double bond?
A. Cl2/light
B.
C. H2SO4
D. cold KMnO4
E. 1. O3 2. DMS
Answer: E
Difficulty: Easy
118. 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
Answer: E
119. 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
Answer: B
120. What is the expected major product of the reaction sequence shown below?
A. I
B. II
C. III
D. IV
E. V
Answer: A
121. What are the expected major products from the reaction sequence shown below?
A. I
B. II
C. III
D. IV
E. V
Answer: A
completion of the following reaction scheme:
Answer:
and

123. 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
Answer: B
Learning Objective: 8.13 List three factors that must be considered in predicting the
products of an addition reaction
Difficulty: Easy
124. The Markovnikov product resulting from an addition reaction to an unsymmetrical

alkene is formed because _____________.
A. the product is statistically favored

B. steric hindrance favors its formation
C. the reaction proceeds via the more/most stable carbocation
D. the reaction forms the more/most stable product
E. All of the above are valid reasons
Answer: C
Difficulty: Easy
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Easy
126. Which reagents are most likely to accomplish the reaction shown below?
A. 1. BH3∙THF / 2. HO–, H2O2, H2O
B. H+, H2O
C. 1. Hg(OAc)2, H2O, THF / 2. NaBH4
D. 1. Hg(OAc)2, CH3OH / 2. NaBH4
E. NaOH, H2O
Answer: A
Difficulty: Easy
127. Which reaction is not stereospecific?
A. I
B. II
C. III
D. IV
Answer: C
Difficulty: Easy
128. Give the expected product(s) resulting from addition of Br2 to (E)-3-hexene.
A. a meso dibromide
B. a mixture of optically active enantiomeric dibromides
C. a mixture of diasteromeric isomers
D. (Z)-3,4-dibromo-3-hexene
E. (E)-3,4-dibromo-3-hexene
Answer: A
129. Which of the following alkenes will yield a meso dihalide when reacted with
Br2/CCl4 at room temperature?
A. I
B. II
C. III
D. IV
E. Both II and IV
Answer: B
130. What is the expected major product resulting from the acid-catalyzed hydration of
2,5-dimethyl-2-hexene?
A. I
B. II
C. III
D. IV
E. V
Answer: B
131. What is the expected major product resulting from treatment of (E)-3-methyl-3-
hexene with Br2 in the presence of methanol, CH3OH?
A. I
B. II
C. III
D. IV
E. All of the above are produced in equal amounts
Answer: B
132. Draw Fischer projection(s) of the major product(s) of the reaction between (Z)-2-
methyl-3-hexene and cold, alkaline KMnO4.
Answer:
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol
product.
133. Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-
methyl-3-hexene and catalytic OsO4 with NMO.
Answer:
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol
product.
134. Predict the structure(s) of the expected major organic product(s) of the following
reaction. Include regiochemical and/or stereochemical details as needed.
Answer:
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity. As
the product is chiral, the products are diastereomers.
135. Identify the best reagents to accomplish a Markovnikov addition of water to an
unsymmetrical alkene with minimal skeletal rearrangement.
A. water and dilute acid

B. water and concentrated acid
C. 1. Hg(OAc)2, H2O 2. NaBH4, NaOH
D. 1. BH3•THF 2. H2O2, NaOH
E. 1. OsO4, pyridine 2. NaHSO3, H2O
Answer: C
Learning Objective: 8.14 Describe mechanisms for changing the positions of a leaving
group or a pi bond
136. For the reaction sequence shown, what is the expected major product?
A. I
B. II
C. III
D. IV
E. V
Answer: D
group or a pi bond
137. What is the expected major product of the following reaction sequence?
A. I
B. II
C. III
D. IV
E. V
Answer: C
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: A
group or a pi bond
139. Which is the correct sequence of steps necessary to complete the following
reaction?
A. I then II then III

B. II then I then III
C. II then IV
D. III then I
E. I then IV then II then III
Answer: B
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: C
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: A
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: C
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: A
group or a pi bond
A. I
B. II
C. III
D. IV
E. V
Answer: C
group or a pi bond
Difficulty: Hard
145. For the following reaction sequence, which molecule is expected as the major
product?
A. I
B. II
C. III
D. IV
E. V
Answer: A + its diastereomer

group or a pi bond
Difficulty: Hard
A. I
B. II
C. III
D. IV
E. V
Answer: E
group or a pi bond
Difficulty: Hard
147. For the following reaction sequence, identify the expected major organic products
and provide their stereochemical relationship.
A. I and II; enantiomers
B. III and IV; enantiomers
C. I and II; diastereomers
D. II and III; diastereomers
E. III and IV; diastereomers
Answer: D
group or a pi bond
Difficulty: Hard
148. A common problem in the acid-catalyzed hydration of alkenes is the formation of

an ether byproduct. Explain the formation of the ether byproduct in relation to the
reaction below:
Answer:
group or a pi bond
149. Starting with (2R,3R)-2-chloro-3,4-dimethylpentane, a) draw the expected major
product for each step, including regiochemical and stereochemical details when
needed. In addition, b) briefly explain the mechanistic rationale for each reaction.
i. t-BuOK/t-BuOH, heat
ii. MCPBA/CH2Cl2
iii. H3O+
Answer:
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.
group or a pi bond
Difficulty: Hard
150. For the following equation a) identify the starting material with correct
stereochemistry and b) provide a complete reaction mechanism, including
stereochemistry, to account for the product shown.
Answer:
Step 1 involves the epoxidation of the (E) alkene by MCPBA, showing only the
enantiomer leading to the given product. Acid-catalyzed ring opening of the epoxide
would occur with regiospecific addition of MeOH to the 3° carbon. Deprotonation by a
general base (“B”, likely MeOH in this example) provides the product, which as can be
seen upon  bond rotation has the same configuration as the product given in the
question.
group or a pi bond
Difficulty: Hard
151. 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 provided with the structure selected.
Answer: A must be 3-ethyl-4-methylcyclopentene. This given data can be

explained as shown below:
group or a pi bond
Difficulty: Hard
152. How many distinct signals would appear in the (proton-decoupled) 13C NMR
spectrum for the product of the following reaction?
A. 3
B. 4
C. 5
D. 6
Answer: B
group or a pi bond + Spectroscopy
Difficulty: Medium
153. 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
Answer: B
group or a pi bond + Spectroscopy
Difficulty: Medium
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PARIS, FRANCE—A SALUTATION FROM M. BLERIOT

One of the first lessons was the “three sixty”—so named because its
completion required a total change in direction of three hundred and
sixty degrees. The cadet would take-off and climb to eight hundred
or a thousand feet. The higher he went the less difficulty he had in
properly completing the maneuver. Then he would fly into the wind
directly over a landing “T” in the center of the field. As the plane
passed over the “T” he throttled his motor and made a quick bank
either to the right or left depending upon his preliminary instructions.
The object was to make a complete circle and land without using the
motor, bringing the plane to a stop beside the “T.”
“One eightys” were the next requirement and they were probably the
cause of more crashes than any other maneuver. They were started
in the same manner as the “three sixty,” but with the plane heading
down wind and at only five hundred feet altitude. They required quick
manipulation of controls and a steep bank into the field just before
landing.
Next came acrobatics. Loops, spins, barrel rolls, Jenny Immelmans,
figure-eights, wing-overs, and reversements, every one of which
each cadet had to master thoroughly during his course at Brooks.
After the first few weeks had passed we became more or less
accustomed to life in the cadet detachment, and found a little time
now and then to look around the country and even spend a night in
San Antonio. Our examinations were purposely given on Saturday
morning so that we would not spend the week-end studying. It was
well known that too much studying affected a cadet’s flying and the
school schedule was arranged with that in mind.
Our day began with first call at five forty-five and flying started about
seven. At eleven we returned to the barracks and from one to five
o’clock was devoted to ground school. After supper we could study
until bed check at ten o’clock. Plenty of sleep is a necessity for the
student pilot, and that fact is recognized nowhere more than in the
army schools. Every week night at ten p.m. the cadet officer of the
day checks each bunk and turns in the names of any vacant ones.
Some of our academic subjects, such as aerodynamics and machine
guns required nearly all of our time after school because of
approaching examinations, whereas others were comparatively easy
and the classroom instruction was sufficient in itself. When we were
not studying there were always plenty of other things to attract our
attention. If one of the boys left the post, as sometimes happened,
he often returned to find his belongings heaped together in the
middle of the floor with the army cots piled on top. Several times
some cadet returned at midnight to find his equipment carefully
transferred and set up on the roof or in the mess-hall. Another one of
the favorite sports was to put a hose in the bed of a sound sleeper at
two a.m. or, if he slept with his mouth open, to fill it from a tube of
shaving cream or hair grease.
One of the fellows found a scorpion in his bed and each night for a
week thereafter looked through the bedding for another, but finally
became careless and forgot to look. His nearest neighbor promptly
placed a number of grasshoppers between the sheets near the foot
of the bed.
Another evening it was reported that three pole-cats had crawled into
a culvert in front of the barracks. For an hour we attempted to smoke
them out. When that failed the fire department was called and we
washed them out. The smoke had evidently taken effect, however,
and soon three dead pole-cats came floating out from the culvert.
The next problem was how to make use of such possibilities. That
question was worthy of a most careful consideration. After a survey
of the barracks we found that our cadet first sergeant was in San
Antonio. There was scarcely one of us who did not have some small
score to settle with him so we took one of the pillows from his bed
and after removing the pillow case, placed it behind one of the pole-
cats. The desired results were then obtained by stepping on the back
end of the cat, and after cautiously inserting the pillow back in its
case, we replaced it on the first sergeant’s bunk. The results were far
above expectation. One by one the occupants of that bay arose and
carried their cots outside, until by midnight, when our sergeant
returned, there were only a half dozen bunks left including his own.
By that time the odor had permeated through the other bedding and
he was unable to locate the pillow as being the primary cause of
offense. Any night for nearly two weeks thereafter our first sergeant
and his cot might be located out behind the barracks, and the
inspection of quarters, which was to have been held the following
morning, was postponed indefinitely.
During our last six weeks at Brooks, life became much less difficult.
Most of us who had survived the check pilots and “Benzine Board”
were reasonably sure of graduating and although our studies were
just as exacting as ever, we were able to absorb them much more
easily. Also we had passed our primary flying tests and were making
cross country flights in T.W.3’s; and learning formation flying in
Voughts. And finally we were given a few hours in De Havilands in
preparation for the advanced training at Kelly.
We were paired up for the cross country flights. One of us flew on
the way out, while the second acted as observer. On the return flight
we traded about, so that each achieved an equal amount of
experience, both as an observer and as a pilot. These trips were
usually laid out in a triangular course, and included landing at each
corner of the triangle.
While on one of our first trips from the home airdrome, we landed in
the designated field alongside of a road just as a load of
watermelons was passing by, so we carried several of them back to
the Detachment in our plane.
Always there was some new experience, always something
interesting going on to make the time spent in Brooks and Kelly one
of the banner years in a pilot’s life. The training is rigid and difficult
but there is none better. A cadet must be willing to forget all other
interest in life when he enters the Texas flying schools and he must
enter with the intention of devoting every effort and all of the energy
during the next twelve months towards a single goal. But when he
receives the wings at Kelly a year later he has the satisfaction of
knowing that he has graduated from one of the world’s finest flying
schools.
VI
RECEIVING A PILOT’S WINGS
IN September, 1924, we were transferred to Kelly. The time we had

looked forward to for half a year had arrived. We were through the
period of just learning how to fly and were entering a new
experience; that of learning how to make use of our flying ability in
actual service. We would no longer be floating around the airdrome
in machines whose only purpose was to stand up under the hard
knocks of inexperienced pilots; but we were going to fly planes which
had an actual military value in warfare.
PARIS, FRANCE—PAUL PAINLEVÉ, FRENCH MINISTER OF

WAR, EXTENDS HIS WELCOME. ON THE RIGHT IS
AMBASSADOR MYRON T. HERRICK
PARIS, FRANCE—WITH M. DOUMERQUE AND AMBASSADOR

HERRICK
We were old cadets and felt the importance of our experience. We

were no longer treated as rookies but as potential officers. Before
leaving Brooks we had conformed with cadet traditions and allowed
groups of the new class to gather around us while we gravely spoke
of examinations, check pilots, “Benzine Boards,” and “washouts.” We
thoroughly enjoyed the awe inspired by our seventy-five hours of
flying experience.
At Kelly our difficulties set in with renewed vigor. The De Havilands
did not maneuver like the training Jennies, and we were required to
fly as we had never flown before. If a cadet was not able to handle
his ship in a maneuver which was at least equal to the standard, he
was usually heading towards home within a week.
We were allowed a few days to become accustomed to flying the
new type of plane, then an instructor would go up with us to see if
our progress had been satisfactory. If so we were sent to the next
stage; if not we went up with a check pilot.
From landings we went to the “eight” stage, where were assigned
two landmarks such as a tree and a haystack several hundred feet
apart, and required to do figure-eights around them. Then came the
spot landing stage, when we throttled our engine at about a
thousand feet and were required to land in a large white circle
without using our motor. On this stage we were graded on our take-
off, climb, approach, landing, roll, distance from mark, and method of
handling the ship. In fact at Kelly we were constantly under
observation and our only method of relaxation while flying was when
the sky was cloudy and we could get above the clouds.
On one occasion we were flying with a low ceiling and the visibility
was not very good. In fact it was an ideal day to do the things we
were not supposed to. I was hedgehopping along over the country
when I saw another D.H. playing around on my right. I flew over, and
after chasing each other around for a while we proceeded to do
chandelles, vertical banks, wing-overs, and everything else we could
think of; all within a few feet of the ground as the clouds themselves
were only about three hundred feet high. At last I decided to go up
close to the other plane for a little low formation flying, but as I
approached I saw that there were two men in the ship and that I had
been breaking every rule ever established about low flying with an
instructor watching me from another ship. I left that locality with wide
open motor and for several days expected to be called on the carpet
before the commanding officer on a washout offense. That instructor
must have been a good sport, however, because I never heard from
him and never was able to find out who he was.
On another occasion, near the end of my course, I came very near
being washed out for something I knew nothing about. I had been
practicing landings in an S.E.-5 on one corner of Kelly Field. When
my time had expired, I landed on the pursuit stage, taxied up to the
line, and turned the ship over to the mechanics. That afternoon I was
called from class and ordered to report to the operations officer;
whereupon he informed me that my flying days were over and that
as I knew why, there was no use in explaining further. I was then
ordered to report back to my studies.
It came out of a clear sky. I knew of a number of offenses I had
committed but none of them at that time. I had actually no idea of
what the operations officer was talking about.
When school was over I returned to the operations hut and
requested an account of the alleged offense. It appeared that the
propeller on my S.E.-5 was cracked, and the spreader board broken
on the landing gear. The crew chief had reported this together with a
statement that there were corn stalks hanging on the landing gear,
and as there was no corn growing on Kelly Field, that was a sure
sign that I had landed away from the airdrome without reporting the
fact. A washout offense. We drove to the pursuit stage and found
conditions exactly as stated, except that the corn stalks turned out to
be weeds, and it was decided that the damage had been caused by
a stake left standing in the corner of Kelly Field where I had been
landing, although I had not felt the ship strike anything. The cadet
who flew the plane earlier in the morning was using the same part of
the field and said that he felt it strike a bump on one of his take-offs
but did not believe any damage had been done. Who was flying the
ship made little difference, however, because as long as he had not
landed away from the airdrome without authority, the slight damage
was of no consequence. I had come very close to the “Benzine
Board” for an offense of which I knew nothing, but it was probably
only the open-mindedness and sense of fair play of the operations
officer that kept me from being washed out as a result.
PARIS, FRANCE—CROWDS AT THE CITY HALL AT THE

OFFICIAL RECEPTION
PARIS, FRANCE—GUESTS AT THE LUNCHEON OF M. BLERIOT

LEFT TO RIGHT: PAUL PAINLEVÉ, CHARLES LINDBERGH, M.
BLERIOT, AMBASSADOR HERRICK
One day during the beginning of our term at Kelly, someone decided
that the cadets should stand reveille. How it came about or who
caused the decision was never known by the detachment, but there
was a strong rumor circulated to the effect that our beloved Cadet
Sergeant had not forgotten the episode of the pole-cats. It was an
unheard of thing for the cadets of Kelly to stand formations. We had
graduated from that when we left Brooks, and the thought of
continuing it in our advanced status was, we concluded,
degenerating to the morale of the detachment.
Consequently, when our first sergeant himself delighted us with
verbal visions of being tumbled out of bed at first call if we were not
up at the blast of his whistle, we decided that if it were in the
combined power of the detachment, the first call should not sound
the next morning. We could not disobey an order; army training
banishes even the remotest thought of that; but we might prevent
that order from being given. The Cadet Captain and first sergeant
were assigned to a private room together. The rest of us were given
cots in the barracks. While supper was in progress that night the
hands on the sergeant’s alarm clock were so manipulated that the
alarm would sound exactly one hour after the time set. At two o’clock
the next morning a padlock was placed on the hasp outside of his
door, and when first call blew a few hours later the cadet detachment
slept soundly on.
From spot landings we passed to hurdles. Hurdles require the ship to
be brought down without assistance from the engine, and after just
passing over a line stretched about eight feet above the ground, to
be landed as close as possible to the hurdle. This gave us excellent
practice for landing over a fence in a small field.
One of the traditions at Kelly was that anyone knocking down the
hurdle must treat the rest to a case of refreshments. It often
happened that a pilot was so intent on getting over the hurdle string
that he did not notice that his plane was in a stall, and about the time
he was over the hurdle the bottom would fall out from under him and
his plane would pancake into the ground. Almost every class had
one or two minor crack-ups as a result of stalling over the hurdle
string.
The De Havilands were not considered safe for hard stunting and as
a result we were only allowed to do wing-overs and split air turns.
Diving in excess of one hundred and fifty miles per hour was also
forbidden. Consequently only air work allowing us to be thoroughly
accustomed to the plane was included in the flying schedule before
our formation training began.
The strange field landing training was one of the most interesting
parts of our schooling. An instructor would lead a number of planes
and land in some field we had never seen before. Then each cadet
was required to land and take-off after the instructor. Some of the
fields were small and full of obstructions. Yet we had comparatively
few even minor crack-ups. Later each cadet was given an
opportunity to lead the rest and pick out a field for them to land in
while the instructor trailed.
At Kelly we were given more and longer cross country trips than at
Brooks. One of the most important parts of flying training is cross
country experience. We made flights to Corpus Christi, Galveston,
Laredo and a number of other places.
Each class spent about two weeks on a gunnery expedition at
Ellington Field between Houston and Galveston. Ellington Field was
one of the few double fields built during the war, but was later
abandoned and, except for a National Guard squadron, was entirely
deserted.
We set up our mess in the clubhouse and made the old building
which had served as officers’ quarters as comfortable as possible.
This was in winter and the weather was cold, even in Texas, unusual
though it might have been. There were no stoves available so we
contrived all sorts of makeshifts to hold a little fire in. If nothing better
was obtainable, we shovelled several inches of earth on the floor
and devised a hood of some kind leading through a few lengths of tin
pipe to the chimney. Of course these fires could not be left
unguarded, so it was necessary to put them out in the morning to be
rekindled at the close of operations for the day.
Our gunnery work was divided into three parts: ground targets,
shadow targets and tow targets. The ground targets were large
sheets of paper similar to those used on a rifle range and were set
up at an angle on the ground. We shot at these with both the
Browning and Lewis machine guns.
The Browning guns on a De Haviland were mounted rigidly in front of
the pilot and were synchronized with the engine to shoot between
the blades of the propeller. They were capable of firing up to twelve
hundred rounds a minute, depending on the motor R.P.M. when they
were fired.
Several of us would form a large circle with our planes, and starting
our dive from about one thousand feet, would fire short bursts into
the target on the ground. After completing our bursts we would zoom
back up into the circle while the next ship started its dive. Each plane
had its individual target.
After emptying the Browning guns we gave our observers a chance
with their Lewises by circling low around the targets. On the next
flight the pilot and observer traded places.
The Lewis gun is mounted on a turret on the rear cockpit. Two guns
were usually used together and they could be pointed in any
direction.
After a few days on ground targets we were sent out over Trinity Bay
for shadow targets. One plane is flown fairly high over the water
while another fires at its shadow. The splashes from the bullets are
easily seen and the accuracy of marksmanship very apparent.
The tow targets are by far the most difficult of the three varieties, and
require skillful maneuvering and excellent marksmanship. They
consist of a cloth sleeve similar to a wind sock which is towed a few
hundred feet behind a De Haviland flying at sixty or sixty-five miles
an hour.
When the forward or Browning guns were used, the attacking ship
approached the tow target head on, firing one or two short bursts as
it passed. In this way there was no danger of the occupants of the
towing plane being struck by a wild shot. The De Havilands were
much too large to use the forward guns effectively on a tow target.
Any accurate shooting required the quick maneuverability of a
pursuit ship.
The Lewis guns were used while flying parallel with the target and
were very effective. When we were close enough we could often see
the tracers pass directly through the cloth sleeve.
After returning from Ellington Field we were given a few hours in
each of the various types of service airplanes. The M.B.-3 and the
S.E.-5 scouts; the Martin Bombers with their twin Liberty engines;
the T.W.-5 two-place transition planes; and the little Sperry
messengers. In this way we obtained experience in each branch:
pursuit, attack, observation and bombardment. Later we were given
our choice of which we desired to specialize in. If our wishes
corresponded with the judgment of the instructors we were assigned
to that branch.
Together with three other cadets and four student officers, I was sent
to the pursuit stage, where we spent the few remaining weeks of our
course, piloting the S.E.-5 and the M.B.-3 single seaters.
Pursuit combines a little of every branch of the air corps. In addition
to formation combat, dog fighting, and ground strafing, the pursuit
pilot is often called upon to make observations and do light bombing.
A great deal of our time was devoted to formation flying. Air combat
of the future will probably often be between large formations rather
than individual pilots, and it is accordingly of utmost importance for
the pursuit pilot to hold his place in formation instinctively, so that his
entire attention can be devoted to the enemy rather than to his own
formation.
We often maneuvered our flights while the individual planes were
less than ten feet apart and it was not unusual to dive vertically for
several thousand feet in a fairly close formation.
We learned the use of Lufberry circles, cross over turns, and other
formation tactics. Our formations were often tight, it is true, but
strange as it may seem, very few accidents occur from too close
flying. A pilot is constantly alert when his plane is only a short
distance from the one in front and nothing is allowed to distract his
attention. On the other hand, when there is quite some distance
separating them he is often more engrossed in lighting a cigarette or
watching some object on the ground than in his own formation.
In pursuit flying we came to have great confidence in our parachutes.
The planes we were flying were kept in excellent condition and none
ever failed, notwithstanding the fact that we placed them under every
conceivable strain imaginable. But the knowledge that we did not
have to concern ourselves about whether they did fall apart or not
was an invaluable factor in building up our morale. Our formations
were tighter, the combats faster, and our flying better as a result.
We had a number of close calls but considering the amount of flying
we had done, and that all of it was military flying, which cannot be
ever compared to commercial traffic as far as safety is concerned,
our accidents were remarkably few and none resulted seriously.
No one knows of the risk he takes better than the pursuit pilot and no
one is less concerned about it. Every move, although at lightning
speed, is made with a coolness born of experience and love of flying.
The army Air Corps is built up of men who fly for the love of flying.
Their only mission in life is to build up the finest air corps in the
world, and their greatest desire is to be given the opportunity to do
so without restriction. If an officer is lost in duty he would be the last
one to wish for resulting restrictions on his comrades.
A week of our pursuit training was spent on a gunnery expedition at
Galveston. We flew there from Kelly Field in M.B.3A. machines and
fired on tow targets exclusively. Our field was close to the Gulf, and
when the day’s operations had been completed we were free to go
about as we chose. Consequently a large part of the evening was
spent along the rocky beach.
On the night of our last day at Galveston several of us were holding
a contest to decide which could reach the most distant rock between
the breakers, before the next wave rolled in. One of the fellows was
outstanding in his accomplishments. In fact he was so dextrous that
none of us could compete, so we were all loud in our praises and
unanimously agreed that there was not a rock in the gulf too obscure
for him. There was, however, a rock a number of feet beyond the
most distant point any of us had attained, which was visible only for
an instant as the last breaker receded and before the next arrived.
Even this was possible, we confidently assured him.
He watched that rock intently for several minutes; then bolstered up
by our praise and his own confidence, he stood poised and ready. At
the proper moment he nimbly leaped from boulder to boulder after
the retreating surf but just before the final rock was touched a large
wave towered above it. Too late! The chance of retreat had never
been considered and its opportunity had passed. With do or die
determination he leaped onto the boulder and into the breaking
wave. This incident would not have been serious or its
consequences important had we been able to carry any extra
equipment in our pursuit planes, but as it was, extra clothing was a
scarce article, and when we took off for San Antonio and Kelly the
following morning, it was necessary for him to send his wet clothes
back in a De Haviland and make his flight in a bearskin flying suit
without insulation against the bearskin.
In warm weather these suits acquired an odor similar to that of a
goat which has been in the barn all winter and the fur itself was far
from comfortable. On the trip back a piston froze in the engine. For
two days the cadet was alternately roasting in the southern sun and
freezing in the Texas nights while he guarded his ship and waited for
a new engine.
After our return from Galveston while we were practicing formation
attack on two seaters, I experienced one of the incidents of the
military pilot’s life. I made my first emergency parachute jump. When
an Army plane crashes, the pilot is required to write a detailed report
of the crash. My account was as follows:
“A nine-ship SE-5 formation, commanded by Lieut. Blackburn, was
attacking a DH4B, flown by Lieut. Maughan at about a 5,000 foot
altitude and several hundred feet above the clouds. I was flying on
the left of the top unit, Lieut. McAllister on my right, and Cadet Love
leading. When we nosed down on the DH, I attacked from the left
and Lieut. McAllister from the right. After Cadet Love pulled up, I
continued to dive on the DH for a short time before pulling up to the
left. I saw no other ship nearby. I passed above the DH and a
moment later felt a slight jolt followed by a crash. My head was
thrown forward against the cowling and my plane seemed to turn
around and hang nearly motionless for an instant. I closed the
throttle and saw an SE-5 with Lieut. McAllister in the cockpit, a few
feet on my left. He was apparently unhurt and getting ready to jump.
“Our ships were locked together with the fuselages approximately
parallel. My right wing was damaged and had folded back slightly,
covering the forward right-hand corner of the cockpit. Then the ships
started to mill around and the wires began whistling. The right wing
commenced vibrating and striking my head at the bottom of each
oscillation. I removed the rubber band safetying the belt, unbuckled
it, climbed out past the trailing edge of the damaged wing, and with
my feet on the cowling on the right side of the cockpit, which was
then in a nearly vertical position, I jumped backwards as far from the
ship as possible. I had no difficulty in locating the pull-ring and
experienced no sensation of falling. The wreckage was falling nearly
straight down and for some time I fell in line with its path and only
slightly to one side. Fearing the wreckage might fall on me, I did not
pull the rip cord until I dropped several hundred feet and into the
clouds. During this time I had turned one-half revolution and was
falling flat and face downward. The parachute functioned perfectly;
almost as soon as I pulled the rip cord the riser jerked on my
shoulders, the leg straps tightened, my head went down, and the
chute fully opened.
“I saw Lieut. McAllister floating above me and the wrecked ships
pass about 100 yards to one side, continuing to spin to the right and
leaving a trail of lighter fragments along their path. I watched them
until, still locked together, they crashed in the mesquite about 2000
feet below and burst into flames several seconds after impact.
PARIS, FRANCE—WITH AMBASSADOR HERRICK ON THE

STEPS OF THE EMBASSY, JUST AFTER ARRIVAL IN PARIS
LONDON, ENGLAND—THE WELCOME AT CROYDEN FIELD

WHERE A MILLING MOB OF NEARLY HALF A MILLION HAD
GATHERED
“Next I turned my attention to locating a landing place. I was over

mesquite and drifting in the general direction of a plowed field which
I reached by slipping the chute. Shortly before striking the ground, I
was drifting backwards, but was able to swing around in the harness
just as I landed on the side of a ditch less than 100 feet from the
edge of the mesquite. Although the impact of landing was too great
for me to remain standing, I was not injured in any way. The
parachute was still held open by the wind and did not collapse until I
pulled in one group of shroud fines.

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Organic Chemistry 10th Edition Carey Test Bank

1. In an addition reaction to an alkene, the π bond is ______.

2. Addition reactions of alkenes are characterized by _________.

4. What is a compound that does not have a double bond?

5. Identify the compound that does not come from an alkene.

6. The alkene precursor to ethanol is __________.

Answer: ethylene or ethene

7. The alkene precursor to acetone is __________.

Answer: propylene or propene

8. Most π bonds are quite prone to reaction with an ____________________, also

10. Which statement best describes the temperature dependence of an addition

A. Addition reactions are thermodynamically favored at all temperatures.

A. The positive entropy dominates at high temperature.

Answer: Vladimir Markovnikov

14. Describe the regioselectivity and stereospecificity in the hydrohalogenation of an

A. Markovnikov orientation with syn-addition

15. In the addition reaction of HI to 2-methyl-2-butene, what is the first step?

A. attack of 2-methyl-2-butene initiated by an iodide ion

19. What compound is the expected product upon Markovnikov hydrohalogenation

20. What is the expected major product of the following reaction?

21. What is the expected major product of the following reaction?

30. Which of the following carbocations is (are) likely to undergo rearrangement

33. What is the major product of the reaction below?

40. When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-

Regioselective addition of the proton of HI generates a secondary carbocation.

A. Markovnikov orientation with syn-addition

43. Give the expected major product of the following reaction.

44. Identify the expected major product of the following reaction.

45. Identify the expected major product of the following reaction.

A. dilute aqueous H2SO4

53. Describe the products of the reaction below.

A. only one stereoisomer

Learning Objective: 8.5 Describe an acid-catalyzed hydration reaction including

Learning Objective: 8.5 Describe an acid-catalyzed hydration reaction including

Learning Objective: 8.5 Describe an acid-catalyzed hydration reaction including

Learning Objective: 8.5 Describe an acid-catalyzed hydration reaction including

A. Markovnikov orientation with syn-addition

59. What synthetic goal is achieved by subjecting an alkene to an oxymercuration-

A. Markovnikov addition of H2O, promoting skeletal rearrangement

64. When an alkene is subjected to treatment with Hg(OAc)2 in alcohol, followed by

66. Any proper mechanism of hydroboration-oxidation must explain the observed

Answer: syn, anti-Markovnikov

A. Markovnikov orientation with syn-addition

Learning Objective: 8.7 Discuss the anti-Markovnikov addition of water across an

75. Identify the product from the hydrogenation of an alkene.

77. What is the name of the product formed when 5-chloro-1-methylcyclohexene is

78. What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C

81. Which alkene would yield 3-methylpentane upon subjection to catalytic

I. Ni II. Pt III. Wilkinson’s catalyst

85. In conducting the catalytic hydrogenation of an alkene, which catalyst listed is

86. Wilkinson’s catalyst accomplishes which of the listed molecular syntheses?

A. syn addition of H2 to an alkene

87. Identify Wilkinson’s catalyst.

89. For the complete reduction of 1 mole of 3E,5E.-hepta-1,3,5-triene with H2 using a

A. Equal amounts of I and II are produced.

96. What major product is expected from the following reaction?