Page 1
1.
What would be the proper name of the following compound?
H3C C C
H3C
C H
OH
A)
1,1-dimethyl-2-propyn-1-ol
B)
3-methyl-1-butyn-3-ol
C)
3-hydroxy-3-methyl-1-propyne
D)
2-methyl-3-butyn-2-ol
E)
2-ethynyl-2-propanol
2.
What would be the product of the following reaction sequence?
H3C C CH ?
1. NaNH2
2. CH3CHO
3. D2O
A)
CH2CCHC
H
DO
CH3
B)
C)
H3C C C CH2CH2OD
D)
H3C C C C CH3
OD
H
E)
CH2CCDC
H
HO
CH3
Page 2
3.
What would be the product of the following reaction?
CH2C C H ?
H2O
cat. H2SO4
cat. HgSO4
A)
CH2CH2C
O
H
B)
CH2C C OH
C)
CH2CH CH2
OH OH
D)
CH2CCH2
OH
E)
O
CH2CCH3
Page 3
4.
What would be the product of the following reaction?
A)
CH2CH2CH2CH3
B)
CH2
C C
CH3
H
H
C)
CH2C C H
D)
CH2
C C CH3
H H
E)
CH2CH2CH2CH3
Page 4
5.
What would be the product of the following reaction sequence?
CH CH 1. Br2
2. excess NaNH
2
?
A)
C C
Br
Br Ph
H
Ph
H
(racemic)
B)
C C
Br
Br Ph
H
Ph
H
(meso)
C)
Ph C C Ph
D)
CH CBr
Ph
Ph
E)
CH CH
NH2
NH2Ph
Ph
6.
Given separate pure samples, in what way(s) could you quickly distinguish between the
two alkynes below?
C C DC C H and
A)
gas chromatography
B)
infrared spectroscopy
C)
ultraviolet spectroscopy
D)
NMR spectroscopy
E)
both B and D
Page 5
7.
What would be the major product expected from the following reaction? (Notice the D
isotope.)
H C C CH CH3
CH3
BD
?
2. H2O2, NaOH
1.
A)
H
C C
CH CH3
CH3
D
HO
B)
H
C C
CH CH3
CH3
OH
D
C)
H3C C
CD CH3
CH3
O
D)
O
C CHD CH
CH3
CH3
H
E)
DH2C C
CH CH3
CH3
O
Page 6
8.
What would you expect the major product of the following reaction sequence to be?
?
H2O
H2SO4
HgSO4
C C H
A)
C
O
CH2CH3
B)
COHC
C)
C
H
C
H
OH
D)
C
O
CH3
E)
C HCH2
O
Page 7
9.
What is the major product expected from the following reaction?
CCH1) NaNH
2 / NH3 (liquid)
2) iodoethane
3) Lindlar‘s catalyst / H
2
?
A)
B)
C)
D)
E)
10.
Considering the mechanism of the following reaction, which of the intermediates shown
below is not likely to form along the reaction pathway?
Na / NH3 (liq)
A)
C C CH3
H3C
B)
H
C)
H
D)
H
E)
C C CH3
H3C
Page 8
11.
What major product(s) are expected from the reaction shown below?
H3C C C CH3HBr (excess) ?
A)
H3C
C C
CH3
HBr
B)
H3C
C C
CH3
Br Br
C)
H3C
C C
CH3
HBr
Br
H
D)
H3C
C C
CH3
HBr
H
Br
E)
more than one of the above
12.
What organic product results from the reaction shown below?
CaC2 + H2O ?
A)
CH4
B)
Ca(CH3)2
C)
CH3CH3 + Ca(OH)2
D)
HC CH
E)
HC
H
OH
OH
Page 9
13.
What is the major product of the following reaction?
1) NaNH2
2)
Br ?
A)
B)
C)
D)
NH2
E)
14.
Which, if either, of the following hydrogenations would be the more exothermic?
H3C C C CH3H2
Pt
H3CC C CH3
H H
H2
Pt CH3CH2CH2CH3
Step 1 Step 2
A)
Step 1
B)
Step 2
C)
both are equally exothermic
D)
neither is exothermic
E)
there is no way to predict this
Page 10
15.
What major product(s) are expected from the reaction shown below?
H3C C C H HI (excess) ?
A)
H3C
C C
H
IH
H
I
B)
H3CC C H
HI
C)
H3C
C C
H
HI
I
H
D)
H3C
C C
H
HI
H
I
E)
H3C
C C
H
II
16.
What reagent(s) would be required to accomplish the transformation shown?
C C CH3
?
CCCH3
H
H
A)
H2, Pt
B)
H2, Lindlar’s catalyst
C)
Na, liq. NH3, then H2O
D)
LiAlH4 then H2O
E)
None of these reagents would accomplish this transformation.
Page 11
17.
What would be the major product of the following reaction?
CH2C C CH3H2?
Pd/C
A)
CH2CH2CH2CH3
B)
CH2
C C
CH3
H
H
C)
CH2C C H
D)
CH2
C C CH3
H H
E)
CH2CH2CH2CH3
18.
What reagent(s) would be required to accomplish the process shown below?
A)
1. HBr
2. NaOH
B)
1. Br2
2. NaNH2 (xs)
C)
1. Br2
2. NaOH
D)
H2SO4
(catalytic)
E)
1. NaNH2
2. H2O
Page 12
19.
Which metal acts as a poison for hydrogenation catalysts?
A)
Pd
B)
Pt
C)
Ni
D)
Pb
E)
Hg
20.
What reactant and product types would be most appropriate for the reagents shown?
1. BH3
2. H2O2, NaOH
? ?
A)
alkene/Markovnikov alcohol
B)
alkene/anti-Markovnikov alcohol
C)
alkyne/aldehyde or ketone
D)
both A and B
E)
both B and C
21.
What is NaNH2 mainly used for in organic chemistry?
A)
as a nucleophile
B)
as a weak base
C)
as a strong base
D)
as a weak acid
E)
as a strong acid
22.
What reagent(s) are required to accomplish the transformation shown?
CCBr
H
H
H?CCD
H
H
H
A)
1. NaD
B)
1. Mg/THF
2. D2O
C)
D2O/peroxides
D)
D2/catalyst
E)
DBr/peroxides
Page 13
23.
What reagent(s) would be required to accomplish the transformation shown?
C C CH3
?
CC
CH3
H
H
A)
H2, Pt
B)
H2, Lindlar’s catalyst
C)
Na, liq. NH3, then H2O
D)
LiAlH4 then H2O
E)
None of the above reagents would accomplish this transformation.
24.
What is the major product from the following reaction?
HgSO4, H2SO4?CH2C C CH3
A)
C C
HO
CH2
CH3
H
B)
C C
HO
CH2
H
CH3
C)
CH2C
O
CH2CH3
D)
E)
no reaction
25.
Infrared spectroscopy is a useful technique in identifying terminal alkynes. What is/are
the characteristic stretching band(s) for a terminal alkyne?
A)
3260-3330 cm-1
B)
1550-1680 cm-1
C)
2100-2260 cm-1
D)
both A and B
E)
both A and C
Page 14
26.
What is the major product of the following reaction?
C CH3C CH3
1. NaOH
2. D2O
?
A)
H3C–CC–CH2D
B)
H3C–CC–CHD2
C)
DH2C–CC–CH2D
D)
D3C–CC–CD3
E)
no reaction
27.
What is the expected product from the following reaction?
C C H
1. n-BuLi
2. D2O / D ?
A)
C C D
B)
C C OD
C)
C C Li
D)
C C C C
E)
no reaction
Page 15
28.
The following is an example of intramolecular Heck reaction. Which product is the most
likely to form?
N
O
Me I
1 mol%Pd(OAc)2
PPh3, NEt3, MeCN
3h, reflux
A)
N
Me
O
B)
N
Me
O
C)
N
OMe
D)
N
Me
O
E)
N
OMe
Page 16
29.
Which product is the most likely to form?
10
H2
Lindlar’s catalyst
A)
10
H
H
B)
10
C)
10
H
H
D)
10
H
Lindlar’s
E)
All of the above will form in nearly equal amounts.
Page 17
Answer Key