ch12 Ques 2013

Chapter 12 Testbank (Klein)- Draft 3
Chapter 12
Topic: One-Step Syntheses
Section: 12.1
Difficulty Level: Easy
1.
Predict the major product(s) for the following reaction:
HBr
Br
Br
A)
B)
C)
D)
E)
Br
Br
IV
III
II
I
II
III
IV
I and III
Ans: E
Chapter 12
Section: 12.1
2.
Provide the reagent(s) required to complete the following transformation:

Br
??
A)
HBr
B)
C)
D)
E)
Br2/h
Br2/ROOR
HBr/ROOR
h /NBS
Ans: D
Chapter 12
Section: 12.1
3.
Br
??
A)
B)
C)
D)
E)
HBr
Br2/h
Br2/ROOR
HBr/ROOR
h /NBS
Ans: E
Chapter 12
Section: 12.1
4.

Br
??
A)
HBr
Br
+ En
B)
C)
D)
E)
Br2/h
Br2
HBr/ROOR
h /NBS
Ans: C
Chapter 12
Section: 12.1
5.

OH
??
+ En
Br
A)
B)
C)
D)
E)
HBr
Br2/H2O
Br2
HBr/ROOR
h /NBS
Ans: B
Chapter 12
Section: 12.1
6.

OH
??
A)
B)
C)
D)
E)
NaOH
heat/H2SO4
CH3CO2H
NaOEt
KOtBu
Ans: B
Chapter 12
Section: 12.1
7.
Predict the major product(s) for the following transformation:
NaSH
Br
SH
HS
Br
A)
B)
C)
D)
E)
Ans: C
Chapter 12
II
I
II
III
IV
I and III
III
HS
IV

Section: 12.1
8.
Predict the reagent(s) required to complete the following transformation:
Br
A)
B)
C)
D)
E)
??
NaOtBu
HBr
H2SO4
NaOH
NaSH
Ans: D
Chapter 12
Section: 12.1
9.
Br
A)
B)
C)
D)
E)
Ans: A
NaOtBu
HBr
H2SO4
NaOH
NaSH
??
Chapter 12
Section: 12.1
10.
Predict the major product(s) obtained from the following reaction:
Cl
DBU
DBU
II
A)
B)
C)
D)
E)
III
I
II
III
IV
II and IV
Ans: C
Chapter 12
Section: 12.1
11.
IV
??
OH
+ En
OH
A)
B)
C)
D)
E)
1) OsO4; 2) NaHSO3, H2O

1) Hg(OAc)2, H2O; 2) NaBH4
1) RCO3H; 2) H3O+
H2SO4, H2O
1) O3; 2) DMS
Ans: C
Chapter 12
Section: 12.1
12.
??
OH
OH
A)
B)
C)
D)
E)

1) RCO3H; 2) H3O+
H2SO4, H2O
1) O3; 2) DMS
Ans: A
Chapter 12
Section: 12.1
+ En

13.
??
A)
B)
C)
D)
E)

1) RCO3H; 2) H3O+
H2SO4, H2O
1) O3; 2) DMS
Ans: E
Chapter 12
Section: 12.1
14.
??
OH
A)
B)
C)
D)
E)

1) RCO3H; 2) H3O+
1) BH3-THF; 2) H2O2, NaOH
1) O3; 2) DMS
Ans: B
Chapter 12
+ En
Section: 12.1
15.
??
+ En
OH
A)
B)
C)
D)
E)

1) RCO3H; 2) H3O+
1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
16.
??
+ En
A)
B)
C)
D)
E)
Ans: C
Chapter 12

H2, Pt
1) O3; 2) DMS

Section: 12.1
17.
??
A)
B)
C)
D)
E)

NaNH2
H2, Pt
Na, NH3(l)
H2, Lindlars catalyst
Ans: D
Chapter 12
Section: 12.1
18.
??
A)
B)
C)
D)
E)

NaNH2
H2, Pt
Na, NH3(l)
H2, Lindlars catalyst
Ans: E
Chapter 12
Section: 12.1
19.
??
H
A)
B)
C)
D)
E)

H2, Pt
1) 9-BBN; 2) H2O2, NaOH
1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
20.

O
??
A)
B)
C)
D)
E)

H2SO4, H2O, HgSO4
H2, Pt
1) 9-BBN; 2) H2O2, NaOH
1) O3; 2) DMS
Ans: B
Chapter 12
Section: 12.1

21.
Na
??
Br
A)
B)
C)
D)
E)
Br

H2SO4, H2O, HgSO4
NaOH
xs NaNH2
1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
22.
??
+ CO2
OH
A)
B)
C)
D)
E)

H2SO4, H2O, HgSO4
NaOH
xs NaNH2
1) O3; 2) H2O
Ans: E
Chapter 12
Section: 12.1
23.
??
n
A)
B)
C)
D)
E)

ROOR, heat
NaOH
xs NaNH2
1) O3; 2) H2O
Ans: B
Chapter 12
Section: 12.1
24.
Br
??
A)
B)
C)
D)
E)

HBr, ROOR
NaBr
xs NaNH2
HBr
Ans: E
Chapter 12
Topic: Functional Group Transformations
Section: 12.2
25.
Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5dimethylhex-1-yne.

A)
B)
C)
D)
E)

HBr, ROOR
NaBr
1) xs NaNH2; 2) H3O+
HBr
Ans: D
Chapter 12
Section: 12.2
Difficulty Level: Medium
26.
Predict the reagent(s) required to convert 1-bromo-1-methylcyclohexane to 1bromo-2-methylcyclohexane.

A)
B)
C)
D)
E)
1) KOtBu; 2) HBr
1) NaOEt; 2) HBr
1) NaOEt; 2) HBr, ROOR
1) KOtBu; 2) HBr, ROOR
Br2, h
Ans: C
Chapter 12
Section: 12.2
27.
Which of the following sequences of reagents will move the alcohol functional
group from the tertiary position of 1-methyl-1-cyclohexanol to a secondary
position?
A)
B)
1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4

1) TsCl, pyr; 2) KOtBu; 3) BH3-THF; 4) H2O2, NaOH
C)
D)
E)
F)
1) H2SO4, heat; 2) BH3-THF; 3) H2O2, NaOH

1) TsCl, pyr; 2) NaOH; 3) BH3-THF; 4) H2O2, NaOH
C and D will both work
A and B will both work
Ans: E
Chapter 12
Section: 12.2
28.
Which sequence of reagents will accomplish the following transformation?
Br
??
A)
B)
C)
D)
E)
1) KOtBu; 2) HBr
1) NaOEt; 2) HBr, ROOR
1) H2SO4, heat; 2) Br2, h
1) NaOEt; 2) HBr
both A and D work
Ans: E
Chapter 12
Topic: Reactions that Change the Carbon Skeleton
Section: 12.3
29.
Which sequence of reagents will accomplish the following transformation?
??
Br
A)
B)
C)
D)
E)
1) KOtBu; 2) 1-bromopropane
1) NaNH2; 2) 1-bromopropane
1) NaNH2; 2) 2-bromopropane
1) O3; 2) DMS
1) O3; 2) 1-bromopropane
Ans: B
Chapter 12
Section: 12.3
30.
Predict the major product(s) for the following reaction:
1) NaNH2
??
2) CH3I
A)
B)
C)
D)
E)
II
III
I
II
III
IV
II and III
Ans: C
Chapter 12
Section: 12.3
31.
Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium
amide followed by reaction with bromoethane.
A)
B)
Hept-1-en-4-yne
Hept-6-en-3-yne
IV
C)
D)
Hept-3-en-6-yne
Hept-4-en-1-yne
Ans: A
Chapter 12
Section: 12.3
32.
Reaction of compound A (molecular formula = C7H12) with sodium amide

followed by reaction with 1-bromobutane produces
(CH3)2CHCH(CH3)CC(CH2)3CH3. What is the name of compound A?
A)
B)
C)
D)
E)
2,3-dimethylnon-4-yne
2,2-dimethylpent-1-yne
3,4-dimethylpent-1-yne
4,4-dimethylhept-1-yne
1-heptyne
Ans: C
Chapter 12
Section: 12.3
33.
Reaction of compound A (molecular formula = C12H22) with ozone followed by

reaction with DMS produces only (CH3)3CCH2CHO. Which of the following
could be compound A?
A)
B)
C)
D)
E)
cis-2,3,7,8-tetramethyloct-4-ene
trans-dodec-6-ene
4,4-dimethylpent-1-ene
cis-2,2,7,7-tetramethyloct-4-ene
2,2-dimethyldec-4-ene
Ans: D
Chapter 12
Section: 12.3
34.
Predict the reagent(s) required to complete the following reaction:
??
HO
OH
O
A)
B)
C)
D)
E)
NaNH2
1) O3; 2) H2O
KMnO4
H2SO4, H2O
Ans: B
Chapter 12
Section: 12.3
35.
Compound X has molecular formula C8H10. Reaction of Compound X with

excess ozone, followed by reaction with dimethyl sulfide and finally rinsing with
water produces only the compounds shown below. Draw a possibility for
Compound X that is consistent with these results.
O
O
Compound X
(C8H10)
1) O3
2) DMS
3) H2O
+
H
O
HO
Ans:
Chapter 12
Section: 12.3
36.
Predict the products of the following reaction:
OH
1) O3
2) DMS
3) H2O
O
C
H
A)
B)
C)
D)
E)
OHC
III
II
OH
IV
COOH
OHC
CHO
VI
I, III, and IV
II, III, and IV
I, III, and V
II, IV, and VI
III and IV
Ans: B
Chapter 12
Section: 12.3
37.
One compound is produced when acetylene is treated with the following reagents.
What is the IUPAC name of this compound?
1) NaNH2
2) 1-bromopropane
3) NaNH2
??
4) 1-bromopropane
5) ozone
6) water
Ans: butanoic acid

Chapter 12
Section: 12.3
38.
Predict a correct sequence of reactants required to complete the following

transformation in which propanal is the only carbon-containing product.
??
NaNH2
I
A)
B)
C)
D)
E)
H2O
II
III
Br
O3
IV
Na/NH3(l)
H2/Pt
VI
VII
1) I; 2) III; 3) IV; 4) V; 5) II
1) VI; 2) IV; 3) IV; 4) VII; 5) V; 6) II
1) V; 2) II
1) I; 2) IV; 3) VI; 4) V; 5) II
none of the above are correct
Ans: D
Chapter 12
Section: 12.3
39.
Propose an efficient synthesis of propanoic acid from acetylene:
Ans:
1) NaNH2
1) O3
2) CH3CH2Br
2) H2O
CO2H
Chapter 12
Topic: How to Approach a Synthesis Problem
Section: 12.4
40.
Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:
??
O
O
Br
Br2, h
1) ozone
KOtBu
2) DMS
Ans:
Chapter 12
Section: 12.4
41.
Identify the changes that must occur in transforming cis-2-butene into 2-butanol:
A)
B)
C)
D)
E)
only the identity of the functional group(s) must change

only the carbon skeleton must change
only the location of the functional group(s) must change
only the identity and location of the functional group(s) must change
both the carbon skeleton and the identity of the functional group(s)
must change
Ans: A
Chapter 12
Section: 12.4
42.
Propose an efficient synthesis of 1-butene from propyne:

1) NaNH2
1) NaNH2
2) MeI
2) H2O
3) H2/Lindlar
Ans:
Chapter 12
Section: 12.4
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
1
2) bromoethane
1) H2, Ni2B
2) BH3-THF
3) H2O2, NaOH
OH
OH
III
II
IV
OH
OH
A)
B)
C)
D)
E)
F)
VII
VI
VIII
Compound 1 = I; Compound 2 = III

Compound 1 = II; Compound 2 = III
Compound 1 = VI; Compound 2 = IV
Compound 1 = II; Compound 2 = IV
Compound 1 = II; Compound 2 = V
Compound 1 = VII; Compound 2 = VIII
Ans: D
Chapter 12
Section: 12.4
44.
Which of the following sequences efficiently converts 2-methylpropene and

sodium acetylide into 3-methylbutanal?
O
??
H
3-methylbutanal
A)
B)
C)
D)
E)
1)
1)
1)
1)
1)
HBr; 2) NaCCH; 3) O3; 4) H2O

HBr; 2) NaCCH; 3) O3; 4) DMS
HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O
HBr, ROOR; 2) NaCCH; 3) H2/Ni2B 3) O3; 4) DMS
NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS
Ans: D
Chapter 12
Section: 12.4
45.
Which of the following sequences most efficiently converts 3-methyl-1-pentene

into 3-bromo-3-methylpentane?
A)
B)
C)
D)
E)
1)
1)
1)
1)
1)
HBr; 2) NaOH; 3) HBr

Br2, h; 2) H2, Pt
H2, Pt; 2) Br2, h
NBS, h; 2) H2, Pt
HBr, ROOR; 2) NaOH; 3) HBr
Ans: C
Chapter 12
Section: 12.4
Difficulty Level: Difficult
46.
Propose a strategy to carry out the following transformation:
??
OH
1) NBS, h
2) H2, Pt
3) NaCCH
4) xs O3
5) H2O
Ans:
Chapter 12
Section: 12.4
47.
Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1butanol.
OH
1) TsCl, pyr
2) KOtBu
3) BH3-THF
4) H2O2, NaOH
Ans:
OH
Chapter 12
Section: 12.4
48.
Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2butanol.

OH
1) H2SO4, heat
2) Hg(OAc)2, H2O
3) NaBH4
Ans:
OH
Chapter 12
Section: 12.4
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?
II
A)
B)
C)
D)
E)
I
II
III
IV
III and IV
Ans: D
III
IV
Chapter 12
Section: 12.4
50.
Which of the following provides an efficient method of converting 3-bromo-2methyl-1-butene into 2-methyl-2-butene?
A)
B)
C)
D)
E)
1)
1)
1)
1)
1)
NaOH; 2) H2, Pt
H2, Pt; 2) NaOEt
H2, Pt; 2) xs NaNH2
H2, Ni2B; 2) KOtBu
H2, Pt; 2) KOtBu
Ans: B
Chapter 12
Section: 12.4
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
Ans: A
Chapter 12
Section: 12.4
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
Ans: B
Chapter 12
Section: 12.4
53.
What is the minimum number of steps required to convert 2-methylpropane into

1-bromo-2-methyl-2-propanol?
A)
B)
C)
D)
E)
1
2
3
4
5
Ans: C
Chapter 12
Section: 12.4
54.
Propose an efficient method of completing the following transformation:
??
OH
+ En
Br
HO
1) NaCCCH3
2) Na/NH3(l)
3) OsO4
Ans:
Br
4) NaHSO3, H2O
Chapter 12
Section: 12.4
55.
??
S
1) 1 Br2, h
2) KOtBu
3) HBr, ROOR
4) NaSMe
Ans:
Chapter 12
Section: 12.4
56.

S
Br
??
Br
Ans:
1) NaOEt
2) NBS, h
3) NaSMe
Chapter 12
Section: 12.4
57.
??
1) Br2
2) xs NaNH2
3) H2O
OH
OH
4) O3
5) H2O
Ans:
Chapter 12
Section: 12.4
58.

Br
??
CHO
Br
Ans:
1) NaCCH
2) 9-BBN
CHO
3) H2O2, NaOH
Chapter 12
Topic: Retrosynthetic Analysis
Section: 12.5
59.
Demonstrate your understanding of retrosynthetic synthesis and determine which

compound(s) could lead immediately to the alkene shown below:
??
Br
A)
B)
C)
D)
E)
F)
III
II
IV
I
II
III
IV
I and IV
I, III, and IV
Ans: E
Chapter 12
Section: 12.5
60.
Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alcohol shown below:
OH
??
A)
B)
C)
D)
E)
F)
II
I
II
III
IV
I and II
I, II, and IV
Ans: E
III
IV
Chapter 12
Section: 12.5
61.
Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alkyne shown below:
??
Br
Br
A)
B)
C)
D)
E)
F)
II
III
Br
Br
IV
Br
I
II
III
IV
I and II
I, II, and IV
Ans: D
Chapter 12
Section: 12.5
62.
Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the alkane shown below:
??
Br
II
III
OH
IV
A)
B)
C)
D)
E)
F)
II and III
I and IV
I
II
III
IV
Ans: B
Chapter 12
Section: 12.5
63.
Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the bromoalkene shown below:
??
Br
OH
Br
Br
A)
B)
C)
D)
E)
F)
II
III
IV
I and III
I and IV
I
II
III
IV
Ans: C
Chapter 12
Section: 12.5
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
C
Br
II
Br
III
IV
OH
Cl
VI
A)
B)
C)
D)
E)
F)
VII
VIII
B = I and A = VI
B = VI and A = I
B = III and A = VII
B = IV and A = VII
B = I and A = III
B = V and A = VIII
Ans: A, D, and E
Chapter 12
Section: 12.5
65.

and B that can lead to the alkyne (C):
C
Br
II
III
Br
Br
Br
IV
OH
Cl
Br
VI
A)
B)
C)
D)
E)
F)
VII
VIII
B = I and A = VI
B = VI and A = I
B = III and A = VII
B = IV and A = VII
B = I and A = III
B = VI and A = VIII
Ans: B
Chapter 12
Section: 12.5
66.

and B that can lead to the alcohol (C):
OH
C
Br
II
Br
III
Br
VI
A)
B)
C)
D)
E)
F)
Br
IV
Cl
Br
Br
VII
VIII
B = I and A = VI
B = VI and A = I
B = III and A = VII
B = IV and A = VII
B = I and A = III
B = VIII and A = V
Ans: D and F
Chapter 12
Section: 12.5
67.

and B that can lead to the compound shown (C):
OH
+ En
OH
OH
II
III
Br
Br
IV
Cl
VI
A)
B)
C)
D)
E)
F)
VII
VIII
B = I and A = VI
B = VI and A = I
B = V and A = II
B = IV and A = VII
B = I and A = III
B = VIII and A = V
Ans: C
Chapter 12
Section: 12.5
68.

and B that can lead to the alkene (C):
HO
Br
III
II
Br
A)
B)
C)
D)
E)
F)
VI
VII
B = I and A = V
B = II and A = VII
B = III and A = I
B = I and A = VII
B = II and A = VI
B = III and A = II
Ans: B and E
Chapter 12
Section: 12.5
69.
Devise a method of converting methylcyclobutane into cyclopentene.
??
1) Br2, h
2) KOtBu
3) BH3-THF
Ans:
4) H2O2, NaOH
5) H2SO4, heat
Chapter 12
Section: 12.5
70.
Devise a method of converting ethylene into PVC (polyvinyl chloride).

1) Br2
2) xs NaNH2
3) H2O
4) 1 eq HCl
5) ROOR, heat
Ans:
Cl
Chapter 12
Section: 12.5
71.
Devise a method of converting acetylene into the polymer shown below.
n
Cl
Ans:
1) NaNH2
2) CH3Br
3) HCl
4) ROOR, heat
Chapter 12
Section: 12.5
72.
Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.

1) Br2
2) xs NaNH2
3) H2O
Ans:
CHO
4) disiamylborane
5) H2O2, NaOH
Chapter 12
Section: 12.5
73.
Devise a method of converting trans-2-methyl-3-hexene into 4-methylpentanoic

acid.
1) Br2
2) xs NaNH2
3) H2O
Ans:
4) ozone
5) H2O
COOH
Chapter 12
Section: 12.5
74.
Which of the following effectively produces 4,4-dimethyl-2-pentyne?
A)
+ NaCCCH3
Br
+ CH3Br
B)
+ 2 NaNH2
C)
Br
D)
Br
+ 1 NaNH2
Br
Ans: B and C
Chapter 12
Section: 12.5
75.
Devise an efficient synthesis of the diol shown below starting with 1,1,3,3tetramethyl-2-ethylcyclohexane.
OH
+ En
OH
1) Br2, h
2) KOtBu
3) HBr, ROOR
Ans:
4) KOtBu
5) Br2
6) xs NaNH2
7) CH3Br
8) H2, Lindlar
9) OsO4
10) NaHSO3, H2O
Chapter 12
Section: 12.5
76.
Devise an efficient synthesis of the diol shown below starting with 1,1,3,3tetramethyl-2-ethylcyclohexane.
OH
+ En
OH
1) Br2, h
2) KOtBu
3) HBr, ROOR
4) KOtBu
5) Br2
6) xs NaNH2
7) CH3Br
8) H2, Lindlar
9) RCO3H
10) H3O+
Ans:
Chapter 12
Section: 12.5
77.
Devise an efficient synthesis of the compound shown below starting with 4methyl-2-pentanol.
OH
O
OH
Ans:
1) TsCl, pyr
2) KOtBu
3) HBr/ROOR
4)
O
ONa
Chapter 12

Section: 12.5
78.
To add one carbon directly to the end of a primary alkyl bromide, one could:
A)
B)
C)
D)
substitute bromide with acetylide, then cleave the triple bond.

substitute bromide with acetylide, then reduce the alkyne to an alkene.
substitute bromide with methoxide.
eliminate hydrogen bromide to produce an alkene.
Ans: A
Chapter 12
Section: 12.5
79.
To remove one carbon from the end of a primary alkyl bromide, one could:
A)
B)
C)
D)
substitute bromide with acetylide, then cleave the triple bond.

substitute bromide with acetylide, then reduce the alkyne to an alkene.
substitute bromide with methoxide.
eliminate hydrogen bromide to produce an alkene, then cleave the
double bond.
Ans: D
Chapter 12
Section: 12.5
80.
Devise a method to complete the following synthesis.
Br
??
+
OH
1) NaOEt
2) BH3-THF
Br
Ans:
OH
3) H2O2, NaOH
OH
Chapter 12
Section: 12.5
81.
acetylene
Ans:
1)
2)
3)
4)
NaNH2
CH3Br
NaNH2
CH3Br
5) H2, Lindlar's catalyst

6) RCO3H
Chapter 12
Section: 12.5
82.
OH
acetylene
+ En
Ans:
1)
2)
3)
4)
NaNH2
CH3Br
NaNH2
CH3Br
5) Na, NH3(l)
6) RCO3H
Chapter 12
Section: 12.5
83.
1) NBS, h
2) HBr, ROOR
Ans:
3) 2 NaCN
Chapter 12
Section: 12.5
84.
Devise a method to prepare 1,7-heptanediol from propene.

1) NBS, h
2) HBr, ROOR
Ans:
3)
4)
5)
6)
2 NaCCH
H2, Lindlar
BH3-THF
H2O2, NaOH
HO
OH
Chapter 12
Section: 12.5
85.
Devise a method to prepare 1,3-dibromopropanol from propene.
Ans:
1) NBS, h
2) Br2, H2O
Br
Br
OH
Chapter 12
Section: 12.5
86.
Devise a method to prepare 3-bromo-1-propanol from propene.
Ans:
1) NBS, h
2) BH3-THF
Br
3) H2O2, NaOH
Chapter 12
Section: 12.5
87.
OH
1) NBS, h
2) KCN
Ans:
N
Chapter 12
Section: 12.5
88.
Devise a synthesis to lengthen the legs of Ralph as requested below.
1)
2)
3)
4)
Ans:
NBS, h
HBr, ROOR
2 NaCCH
H2, Pt

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Chapter 12 Testbank (Klein)- Draft 3

Predict the major product(s) for the following reaction:

Provide the reagent(s) required to complete the following transformation:

Provide the reagent(s) required to complete the following transformation:

Provide the reagent(s) required to complete the following transformation:

Provide the reagent(s) required to complete the following transformation:

Provide the reagent(s) required to complete the following transformation:

Predict the major product(s) for the following transformation:

Topic: One-Step Syntheses

Predict the reagent(s) required to complete the following transformation:

Predict the reagent(s) required to complete the following transformation:

Predict the major product(s) obtained from the following reaction:

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Difficulty Level: Easy

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Topic: One-Step Syntheses

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Difficulty Level: Easy

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to complete the following transformation:

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5dimethylhex-1-yne.

1) OsO4; 2) NaHSO3, H2O

Predict the reagent(s) required to convert 1-bromo-1-methylcyclohexane to 1bromo-2-methylcyclohexane.

1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4

1) H2SO4, heat; 2) BH3-THF; 3) H2O2, NaOH

Which sequence of reagents will accomplish the following transformation?

Which sequence of reagents will accomplish the following transformation?

Predict the major product(s) for the following reaction:

Reaction of compound A (molecular formula = C7H12) with sodium amide

Reaction of compound A (molecular formula = C12H22) with ozone followed by

Predict the reagent(s) required to complete the following reaction:

Compound X has molecular formula C8H10. Reaction of Compound X with

Predict the products of the following reaction:

Ans: butanoic acid

Predict a correct sequence of reactants required to complete the following

Propose an efficient synthesis of propanoic acid from acetylene:

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

only the identity of the functional group(s) must change

Propose an efficient synthesis of 1-butene from propyne:

The following sequence of reactions transforms acetylene into a compound with