Page 1
1.
What would be the product of the following reaction?
O
CH3
HCH3OH
H+
?
A)
OH CH3
H
OCH3
B)
HOH
CH3O
CH3
C)
OH H
CH3O
CH3
D)
HOH
H3C
OCH3
E)
OH
HCH2
2.
What would be the product of the following reaction?
A)
CO2 + H2O
B)
OOH
CH3CH OCH2CH3
C)
OOHCH3CH2OCH2CH2
D)
O OCH3CH2CH2CH3
E)
CH3CH2OCH2CH2OH
Page 2
3.
Which of the following would you expect to have the lowest boiling point?
A)
CH3CH2OH
B)
CH3CH2SH
C)
CH3OCH3
D)
CH3SCH3
E)
The boiling points would be the same.
4.
What reagent would best accomplish the following reaction?
CH2CH2OH CH2CH2Br
?
A)
Br2
B)
NaBr
C)
CH3Br
D)
NH4+ Br–
E)
PBr3
Page 3
5.
What would be the expected product of the following reaction?
SH
?+ I2
A)
SS
B)
I
C)
(trans)
D)
(cis)
E)
SO
O
OH
6.
What would be the expected product(s) of the following reaction?
CH3CH2CH2CH2OCH2CH2CH2CH3?
HI (excess)
heat
A)
CH3CH2CH2CH2OH + CH3CH2CH2CH2I
B)
CH3CH2CH2CHI-O-CH2CH2CH2CH3
C)
2 CH3CH2CH2CH2I
D)
CH3CH2CH2CH2OCH2CH2CH2CH3
H
+ I–
E)
no reaction occurs
Page 4
7.
What would be the major organic product from the following reaction?
H
CCH3
H3C
C
OH
CH3
H
?
HCl (conc)
A)
H
CCH3
H3C
CCl
CH3
H
B)
H
CCH3
H3C
C
H
CH3
Cl
C)
H
CCH3
H3C
CCl
CH3
H
(racemic)
D)
Cl
C
CH3
H3C
C
H
CH3
H
E)
C
H3C
H3C
C
CH3
H
8.
What would be the best name of the following compound?
O
A)
3-methyl-4-oxohexane
B)
2-butoxyethane
C)
1-methy-1-ethoxypropane
D)
(1-ethyl)-diethylether
E)
2-ethoxybutane
Page 5
9.
What significant characteristic(s) does diethyl ether exhibit?
A)
It functions as an anesthetic.
B)
It is extremely flammable.
C)
It is a common solvent.
D)
It can react slowly with oxygen at room temperature.
E)
All of the above are true.
10.
Which of the following reactions would be the best for the preparation of anisole
(methoxybenzene)?
OCH3
A)
Br
?
CH3O– Na+
B)
OH
?
CH3OH
H2SO 4
C)
O– Na+
?
CH3Br
D)
O?
1. CH3MgBr
2. H3O+
E)
None of the above would work.
Page 6
11.
Which of the following reactions would be best for the preparation of Nerolin II?
OCH2CH3
Nerolin II
(odor of orange blossoms)
A)
OH
?
CH3CH2OH
H2SO 4
B)
O– Na+
?
CH3CH2Br
DMSO
C)
Br CH3CH2O– Na+
DMSO
?
D)
Any of the above would work.
E)
None of the above would work.
Page 7
12.
What would be the product of the following reaction?
O
H
H?
CH3S– K+
A)
OH
H
H
SCH3
B)
OH
H3CS
H
H
C)
OH
H
H
SCH3
D)
OSCH3
H
H
H
E)
OH
H
Page 8
13.
What product would result from the following reaction?
O?
HBr (excess)
heat
A)
O
Br
B)
OH
Br
C)
OBr
D)
Br
OH
E)
Br
Br
Page 9
14.
What would be the product of the following reaction?
OH 1) KH
2) CH3I?
A)
OCH3
B)
C)
D)
CH3
E)
OH
Page 10
15.
In the following reaction, an interesting rearrangement takes place. Suggest a structure
for the product that is obtained.
Conc. HCl
OH
?
A)
B)
Cl
C)
D)
Cl
E)
Cl
Page 11
16.
What is the product of the following reaction?
OH 1) TsCl / pyridine
2) NaCN ?
A)
OTs
B)
C)
Cl
D)
CN
E)
NC
Page 12
17.
What is the major product of the following reaction?
OH
H2SO4?
heat
A)
B)
C)
O
D)
E)
18.
Ethers have lower boiling points than comparable alcohols because:
A)
they are able to complex with the metal, magnesium.
B)
they do not contain a carbonyl group.
C)
the oxygen of the ether is sp2 hybridized.
D)
they are not able to hydrogen bond with themselves.
E)
they have more acidic protons than alcohols.
Page 13
19.
Which reagent(s) would accomplish the following reaction?
OOH
?
A)
H2O, H+
B)
NaH
C)
1. LiAlH4
2. H2O
D)
NaOH, H2O
E)
1. CH3MgBr
2. H2O
20.
What is the major product of the following reaction?
Cl OH NaOH ?
A)
HO OH
B)
O
C)
Cl
D)
O
E)
O
Page 14
21.
When considering the mechanism of the following reaction, which of the following
statements is true?
OH O
H2SO4
A)
A molecule of water is lost.
B)
The mechanism involves an SN2 reaction.
C)
A free carbocation is formed.
D)
An alkoxide is involved as a nucleophile.
E)
Both A and C are true.
22.
What is the major product of the following reaction:
OH
O
CH3OH H+
+?
A)
O
O
O
B)
OH
OCH3
C)
H
O
D)
OCH3
O
E)
O
Page 15
23.
What is the major product of the following reaction:
OH H2SO4?
A)
OSO3H
B)
C)
D)
E)
None of the above.
Page 16
24.
What is the major product of the following reaction?
H3C H
OHH H , CH3OH ?
A)
HO
B)
OCH3
HO
C)
H3CO
HO
D)
H3CO OH
E)
OH
Page 17
25.
What is the major product of the following reaction?
H3C H
OHH 1) CH3CH2MgBr , Et2O
2) H3O
?
A)
HO
B)
OH
C)
OH
D)
OOH
E)
OOH
26.
Which set of reagents will effect the following transformation?
OH
O
O
O
?
A)
benzoic acid / H3O+
B)
OH
, H+
C)
MCPBA
D)
butanoic acid / H3O+
E)
CH3CH2OH / H3O+
Page 18
27.
What is the major product of the following reaction?
Et
Me
OH
H2SO4 / 185 oC?
A)
Et
Me
B)
Et
Me
C)
Et
D)
Et
Me
E)
Me
28.
What type of reaction will happen to phenol upon treatment with catalytic sulfuric acid?
OH
A)
E1
B)
E2
C)
Free-radical elimination
D)
Electrophilic elimination
E)
A reaction will not take place.
Page 19
29.
What is the structure of THF?
A)
O
B)
O
O
C)
O
D)
O
E)
O
30.
Which type of inorganic esters tends to be shock-sensitive (explosive)?
A)
Phosphate
B)
Nitrate
C)
Phosphite
D)
Sulfate
E)
Tosylate
31.
Diethyl ether can be dangerous for which of the following reasons:
A)
It is highly toxic.
B)
It tends to slowly accumulate hydroperoxides.
C)
It is extremely flammable.
D)
All of the above.
E)
Two of the above.
32.
Crown ethers are important because they
A)
have antibiotic properties.
B)
have the ability to dissolve certain salts in organic solvents.
C)
occur in marine organisms.
D)
promote the oxidation of certain organics.
E)
are used as binders in detergent formulations.
Page 20
33.
Which of the following reactions would produce diethyl ether?
A)
H2SO 4
heat
CH3CH2OH
B)
NaOH
CH3CH2Br
C)
CH3CH2ONa
CH3CH2Br
D)
All of the above.
E)
Two of the above.
34.
Which of the following is true of thiols?
A)
They are more acidic than alcohols.
B)
They have lower boiling points than the corresponding alcohol.
C)
Thiol oxidations proceed very differently than alcohol oxidations.
D)
All of the above.
E)
Two of the above.
Page 21
35.
The Merck Index reports that the odor of geosmin can be detected at 0.1 parts per
billion, but that it is quickly converted to essentially odorless products in acidic solution.
What is the expected major product of treatment of geosmin with sulfuric acid?
CH3
CH3
HO
geosmin
A)
CH3
CH3
B)
CH3
H3C
C)
CH3
CH3
D)
CH3
CH3
E)
CH3
CH3
Page 22
36.
Which of the following is a reasonable method of synthesizing methoxide?
A)
CH3OH + LDA
B)
CH3OH + nBuLi
C)
CH3OH + KH
D)
Two of these are reasonable methods.
E)
All of these would work.
37.
Predict the major product of the following reaction
OH
HBr
A)
Br
B)
Br
C)
Br
D)
A and B in equal proportions
E)
B and C in equal proportions
Page 23
38.
Predict the major product of the following reaction: 2,3-dimethylcyclohexanol +
H2SO4
A)
HO
B)
C)
HO3S
D)
E)
OH
39.
Give the IUPAC name for the following compound:
OCH2CH3
OCH3
A)
1-ethoxy-2-methoxycyclobutane
B)
1-ethoxy-2-methoxycyclopropane
C)
1-methoxy-2-ethoxycyclobutane
D)
1-methoxy-2-ethoxycyclopropane
E)
1-methoxy-2-ethoxybutane
Page 24
40.
Predict the major product of the following reaction:
Br OH KOH
A)
O
B)
Br CHO
C)
D)
O
E)
HO OH
Page 25
41.
Predict the major product of the following reaction:
Br
HO CH2CH3
KOH
A)
OCH2CH3
B)
OCH2CH3
C)
OCH2CH3
D)
O
Racemic Mixture
E)
42.
For the transformations below, what is the structure of the starting material?
1) CH3CH2CH2Li
2) H3O+, H2O
CH3CH2CH2CH2CH2OH
?
A)
CH3CH2OH
B)
O
H3C H
C)
O
H3C OEt
D)
O
E)
None of the above.
Page 26
43.
For the transformations below, what is the structure of the product?
O
CH31) LiAlH4, (CH3CH2)2O
2) H3O+, H2O
A)
CH3
OH
B)
CH3
OH
C)
CH3
OH
D)
CH3
OH
OH
E)
None of the above.
44.
For the transformations below, what is the structure of the major product?
OH
Br
NaH, DMF
A)
ONa
Br
B)
O
C)
O
D)
OH
H
E)
OH
Page 27
45.
For the transformations below, what is the structure of the starting material?
HO
Li
1.
2. H3O+
?
A)
O
H H
B)
CH3CH2OH
C)
O
H CH3
D)
O
E)
O
46.
Predict the major product if the following reaction went by the SN1 pathway:
Cl
CH3CO2H?
A)
O2CCH3
B)
O2CCH3
C)
D)
O2CCH3
E)
O2CCH3
Page 28
47.
Which of the sequences below would accomplish the following transformation?
CH2OH CH2D
?
A)
1. HBr
2. NaBD4, CH3OH
B)
1. PBr3
2. Mg, ether
3. D2O
C)
D2SO4
D)
1. LiAlD4
2. H3O+
E)
1. H2SO4
2. D2, catalyst
Page 29
Answer Key
Page 30