Page 1
1.
What would be the organic product of the following reaction?
H2C
O
CH2
O
O
O
O
O
H3O+
heat ?
A)
2 HO2CCH2CO2H
B)
2 CH3C(=O)CH3
C)
2 CH3CO2H
D)
HO2CCH2C(=O)O2CCH2C(=O)O2CCH2CO2H
E)
No reaction occurs.
2.
What product would result from the following reaction sequence?
H3C C CH2C
O O
OCH2CH3
1. NaOCH
2CH3
2. C6H5CH2Br
3. H3O+, heat ?
A)
H3C C CH2
O
C6H5
B)
C)
HO CCH2
O
C6H5
D)
H3C C CH2
O
CH2C6H5
E)
H3C C CH C
O O
OCH2CH3
CH2C6H5
Page 2
3.
To which side, if any, would the following equilibrium lie?
O O OH O
A)
To the left
B)
To the right
C)
Equally to the left and right
D)
Reaction cannot occur at all
E)
Equilibrium favors a different product
4.
Which of the following would be the most acidic?
A)
O
B)
CH3CH2CO2CH3
C)
O
O
D)
O O
E)
O
CH3
Page 3
5.
Predict the products of the following reaction.
CO2H
CO2H
O?
heat
A)
CO2H
O
B)
CO2H
O
CO2H
+
C)
CO2H
D)
O
E)
None of these.
Page 4
6.
What would be the expected product of the following reaction sequence?
H3C C
O
OCH2CH3
1. CH3CH 2O– Na+
2. H3O+ (no heat) ?
A)
H3CCH2OCH2CH3
OO
B)
H3C O OCH2CH3
O O
C)
H3CCCH2C OCH2CH3
OH O
H
D)
H3C C
O
OH
E)
CH3CH2O C
O
C
O
OCH2CH3
7.
What factors contribute to the stability of the following structure?
H3CCCCCH3
OHO
H
A)
structure has a 6 electron aromatic system
B)
stabilized by conjugation between C=C and C=O
C)
C=C is generally more stable than C=O
D)
structure has intramolecular hydrogen bonding
E)
More than one of the above are true.
8.
The Dieckmann reaction is best described by which of the following statements?
A)
Intermolecular Aldol Condensation
B)
Intramolecular Aldol Condensation
C)
Intermolecular Claisen Condensation
D)
Intramolecular Claisen Condensation
E)
Michael Addition followed by intramolecular Aldol
Page 5
9.
Why is the following reaction typically done?
S
C
S
H3CH
C
H3CH
OHSCH2CH2CH2SH
HCl
A)
To protect the aldehyde against oxidation
B)
To render the molecule inert to organometallic reagents
C)
To make the aldehyde CH more acidic
D)
To render the molecule more fragrant
E)
To protect the aldehyde against reduction
10.
Predict the major organic product of the following reaction.
O
O+ O
O1) NaOEt
2) H3O?
A)
O
O
O
B)
O
O
O
O
C)
O
O
D)
O
O
O
E)
The reaction does not occur.
Page 6
11.
What product would be expected to result from the reaction sequence shown?
H3CH2CO OCH2CH3
O O 1. NaOCH2CH3
2. CH3CH2CH2CH2Br
3. NaOH, H
2O, heat
4. H3O+, heat
?
A)
H3CH2CO CH2CH2CH2CH3
O O
B)
H3CH2CO OCH2CH3
O O
CH2CH2CH2CH3
C)
D)
HO OH
O O
CH2CH2CH2CH3
E)
HO2C–CH2CH2CH2CH2CH3
Page 7
12.
Which of the following reaction sequences will affect the following transformation?
H
O?O
OH
A)
1) n-BuLi / THF
3) H3O+
O
H
2)
B)
1) n-BuLi / THF
4) H3O+
O
H
3)
2) N, H+
C)
1) NaH / THF
3) H3O+
2)
O
D)
2) n-BuLi / THF
1) HSCH2CH2CH2SH /ZnCl2
O
H
3)
4) H3O+
5) HgCl2 / H2O / CaCO3 / CH3CN
Page 8
E)
P
1)
2) H3O+
13.
Predict the major product of the following reaction?
O
O1) NaOEt / EtOH
2) H3O+?
A)
O
O
O
B)
O O
C)
O
O
O
D)
O
O
OH
E)
No significant reaction occurs.
Page 9
14.
Predict the major organic product of the following reaction.
O
O
+
O NaOEt / EtOH ?
A)
O
O
B)
O
O
C)
O
O
OH
D)
O
O
E)
O
O
Page 10
15.
What would result from the reaction shown below?
O
CH3
H3C
OCH2CH3
OCH3CH2ONa
CH3CH2OH ?
A)
O
CH3
H3C
H
B)
CH3CH2O
O
CH3
H3C
OCH2CH 3
O
C)
OCH2CH 3
O
2
D)
O
CH3
H3C
ONa
O
E)
O
OCH2CH 3
OO
Page 11
16.
What missing reactant would be required to provide the product shown?
H3C C
O
OCH3
1. CH3ONa, CH 3OH
2. H3O+
+ ? C C
O
OCH3
C
O
H
HH
A)
H C
O
OCH3
B)
H C
O
CH2Cl
C)
H2C O
D)
CH3O C
O
OCH3
E)
None of these would work.
17.
What problem is encountered in the synthesis of ethyl acetoacetate (shown below) if
sodium methoxide is used rather than sodium ethoxide?
C C
O
OCH2CH3
C
O
H3C
HH
H3C C
O
OCH2CH3
21. RO– Na+
2. H3O+
ethyl acetoacetate
?
A)
Sodium methoxide is too weak a base to cause this reaction to occur.
B)
The condensation proceeds further to give tri-carbonyl products.
C)
The reaction would produce some of both the methyl ester and the ethyl ester.
D)
Sodium methoxide is too insoluble in methanol to promote the reaction.
E)
Sodium methoxide is not basic enough to drive the reaction to completion.
Page 12
18.
Predict the major product of the following reaction.
O O
O O 1) NaOEt / EtOH
2) CH3CH2CH2Br
3) KOH / H
2O / heat
4) H2SO4 / H2O / heat
?
A)
O O
O O
B)
OOH
O O
C)
OH
O
D)
E)
HO OH
O O
Page 13
19.
Which of the following compounds will not readily undergo decarboxylation (loss of
CO2) upon heating in an appropriate solvent?
A)
OH
O O
B)
O
O
OH
C)
HO
O O
D)
HO
OOH
E)
HO OH
O O
Page 14
20.
Predict the major product of the following reaction.
O
O
OO
+NaOEt / EtOH ?
A)
O
O
O
B)
OOO
C)
O
O
O
OH
D)
O
O
O
O
E)
O
O
O
Page 15
21.
What would be the expected product of the following reaction sequence?
H3C C
O
OCH2CH3
1. CH3CH2O– Na+
2. H3O+ and heat ?
A)
H3CCCH2
COCH2CH3
OO
B)
H3C C CH2C OH
O O
C)
H3C C CH2C OEt
OH O
H
D)
H3C C
O
CH3
E)
H3C C
O
OH
22.
Which of the following processes involves loss of one carbon as carbon dioxide?
A)
Claisen condensation
B)
Michael addition
C)
Malonic ester synthesis
D)
None involve loss of CO2.
E)
All involve loss of CO2.
23.
Which would be the most acidic proton in the molecule below?
O
O
H
H
HH
HO
H
H
H
a
b
c
d
e
A)
Protons a
B)
Proton b
C)
Proton c
D)
Protons d
E)
Protons e
Page 16
24.
After treatment with aqueous base + heat, followed by acidification to pH 2 followed by
heating, which carbon in the molecule below would be lost as carbon dioxide?
H3CO C
O
CH2C
O
CH2CH2C
O
O CH2CH3
a
bc
d
e
A)
Carbon a
B)
Carbon b
C)
Carbon c
D)
Carbon d
E)
Carbon e
25.
Which of the indicated hydrogens would be the most acidic?
H3C C
O
CH2C
O
CH2C
O
O CH2CH3
a
bc
d
e
A)
Hydrogens a
B)
Hydrogens b
C)
Hydrogens c
D)
Hydrogens d
E)
Hydrogens e
Page 17
26.
What product do you expect from the following reaction?
O
O
CH3CH2O Na
heat ?
A)
O
B)
O
C)
D)
Some of these would be formed.
E)
None of these would be formed.
Page 18
27.
What product do you expect from the following reaction?
CH3O-C-CH2CH2CH2CH2-C-OCH3
O O 1) CH3ONa
2) H3O+
A)
OCH3
O
O
B)
O
O
C)
OCH3
OO
D)
OCH3
O
O
OCH3
E)
O
O
O
Page 19
28.
What product do you expect from the following reaction?
A)
O
CN
B)
CH3
OO
CN
C)
O
CN
D)
OO
CN
E)
CH3
OO
NC
Page 20
29.
What product do you expect from the following reaction?
OHC-CH2CH2CH2CH2-CHO NaOH
N
S
(CH2)11CH3
Br–
A)
OH
CHO
B)
O
CHO
C)
O
O
D)
OH
O
E)
no reaction
Page 21
Answer Key