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41. Identify the changes that must occur in transforming cis-2-butene into 2-butanol:
A) only the identity of the functional group(s) must change
B) only the carbon skeleton must change
C) only the location of the functional group(s) must change
D) only the identity and location of the functional group(s) must change
E) both the carbon skeleton and the identity of the functional group(s)
must change
42. Propose an efficient synthesis of 1-butene from propyne:
43. The following sequence of reactions transforms acetylene into a compound with
an altered carbon skeleton (compound 1), and from that into a compound in which
the functional group has been changed (compound 2). Identify compounds 1 and
2:
1) NaNH2
2) bromoethane
11) H2, Ni2B
2) BH3-THF
3) H2O2, NaOH
OH
OH
OH
OH
2
III III IV
VVI VII VIII
A) Compound 1 = I; Compound 2 = III
B) Compound 1 = II; Compound 2 = III
C) Compound 1 = VI; Compound 2 = IV
D) Compound 1 = II; Compound 2 = IV
E) Compound 1 = II; Compound 2 = V
F) Compound 1 = VII; Compound 2 = VIII
44. Which of the following sequences efficiently converts 2-methylpropene and
sodium acetylide into 3-methylbutanal?
H
O
3-methylbutanal
??
A) 1) HBr; 2) NaCCH; 3) O3; 4) H2O
B) 1) HBr; 2) NaCCH; 3) O3; 4) DMS
C) 1) HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O
D) 1) HBr, ROOR; 2) NaCCH; 3) H2/Ni2B 3) O3; 4) DMS
E) 1) NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS
45. Which of the following sequences most efficiently converts 3-methyl-1-pentene
into 3-bromo-3-methylpentane?
A) 1) HBr; 2) NaOH; 3) HBr
B) 1) Br2, h; 2) H2, Pt
C) 1) H2, Pt; 2) Br2, h
D) 1) NBS, h; 2) H2, Pt
E) 1) HBr, ROOR; 2) NaOH; 3) HBr
46. Propose a strategy to carry out the following transformation:
?? O
OH
47. Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-
butanol.
48. Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-
butanol.
49. Which of the following alkenes cannot be converted into an alkyne by reaction
with bromine followed by excess sodium amide and then with water?
III III IV
A) I
B) II
C) III
D) IV
E) III and IV
50. Which of the following provides an efficient method of converting 3-bromo-2-
methyl-1-butene into 2-methyl-2-butene?
A) 1) NaOH; 2) H2, Pt
B) 1) H2, Pt; 2) NaOEt
C) 1) H2, Pt; 2) xs NaNH2
D) 1) H2, Ni2B; 2) KOtBu
E) 1) H2, Pt; 2) KOtBu
51. Which order of alterations would most effectively transform trans-2-butene into
1-butene?
A) convert to the dibromoalkane, then to the terminal alkyne, then to the
terminal alkene
B) convert to an alcohol, then to a terminal alkyne, finally to the terminal
alkene
C) convert to the terminal alkene in one step
D) shorten the chain by two carbons, then add a two-carbon alkene to the
end
E) convert to an alkane, then to a terminal alkyne, and finally to a terminal
alkene
52. What is the minimum number of steps required to convert 2-methylpropane into
2-methylpropene?
A) 1
B) 2
C) 3
D) 4
E) 5
53. What is the minimum number of steps required to convert 2-methylpropane into
1-bromo-2-methyl-2-propanol?
A) 1
B) 2
C) 3
D) 4
E) 5
54. Propose an efficient method of completing the following transformation:
Br
??
HO
OH
+ En
55. Propose an efficient method of completing the following transformation:
??
S
56. Propose an efficient method of completing the following transformation:
Br
??
S
57. Propose an efficient method of completing the following transformation:
OH
O
??
58. Propose an efficient method of completing the following transformation:
Br
CHO
??
59. Demonstrate your understanding of retrosynthetic synthesis and determine which
compound(s) could lead immediately to the alkene shown below:
??
Br
I II III IV
A) I
B) II
C) III
D) IV
E) I and IV
F) I, III, and IV
60. Using retrosynthetic synthesis, determine which compound(s) could lead
immediately to the alcohol shown below:
OH
??
I II III IV
A) I
B) II
C) III
D) IV
E) I and II
F) I, II, and IV
61. Using retrosynthetic synthesis, determine which compound(s) could lead
immediately to the alkyne shown below:
??
Br
I II III IV
Br Br
Br
Br
A) I
B) II
C) III
D) IV
E) I and II
F) I, II, and IV
62. Using the concept of retrosynthetic synthesis, determine which compound(s)
could lead immediately to the alkane shown below:
??
I II III IV
Br OH
A) II and III
B) I and IV
C) I
D) II
E) III
F) IV
63. Using the concept of retrosynthetic synthesis, determine which compound(s)
could lead immediately to the bromoalkene shown below:
Br ??
Br Br
OH
I II III IV
A) I and III
B) I and IV
C) I
D) II
E) III
F) IV
64. Show that you understand the concept of retrosynthetic analysis by working
backwards two steps in the synthesis below. Identify possible combinations of A
and B that could lead to the alkyl halide (C):
Br
BA
C
Br
I II III IV
VVI VII VIII
OH
Br
Cl
A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = I and A = III
F) B = V and A = VIII
65. Show that you understand the concept of retrosynthetic analysis by working
backwards two steps in the synthesis below. Identify possible combinations of A
and B that can lead to the alkyne (C):
BA
C
Br
I II III IV
VVI VII VIII
OH
Br
Cl
Br
Br
Br
A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = I and A = III
F) B = VI and A = VIII
66. Show that you understand the concept of retrosynthetic analysis by working
backwards two steps in the synthesis below. Identify possible combinations of A
and B that can lead to the alcohol (C):
BA
C
Br
I II III IV
VVI VII VIII
Br
Cl
Br
Br
Br
OH
Br
A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = I and A = III
F) B = VIII and A = V
67. Show that you understand the concept of retrosynthetic analysis by working
backwards two steps in the synthesis below. Identify possible combinations of A
and B that can lead to the compound shown (C):
