Page 1
1.
Which product would you not expect in the crossed aldol reaction between acetaldehyde
and propionaldehyde?
H3CC
O
HCH2C
O
H
H3C?
cat. NaOH
H2O
+
A)
CH2C
O
H
H2C C
OH
H
H3C
B)
CH C
O
H
H3C C
CH3
H
OH
C)
CH2C
O
H
H3CC
OH
H
D)
CH C
O
H
H3C C
OH
HCH3
E)
CH C
O
H
H2C C
OH
HCH3
H3C
Page 2
2.
What organic molecule would you expect to be present in significant amounts under
the following conditions?
O
CH3
H
cat. KOD ?
only (S) enantiomer
excess D2O
A)
DO
CH3
H
OH
B)
O
CH3
D
C)
O
D)
OCH3
D
racemic
E)
OCD3
D
racemic
Page 3
3.
What reactants would be used to produce cinnamaldehyde?
CHO
?cat. NaOH
H2O
A)
CHO + CH3CHO
B)
CHO
HCCHO
O
+
C)
CH3
O
+ CH2=O
D)
OCHO
+
E)
CHO
H3CCCHO
O
+
Page 4
4.
What would you expect to result from the following reaction?
O?
1. (CH3)2CuLi
2. H2O
A)
O
B)
OH
C)
OH
CH3
D)
O
E)
O
Page 5
5.
Indicate to which side, if any, the following equilibrium lies:
O O
H+ or HO–
A)
To the right
B)
To the left
C)
Equally to right and left
D)
Cannot be predicted
E)
Major product is an enol or enolate ion, respectively
Page 6
6.
What would be the expected product of the following reaction?
CH3
O
HC
CH2
O
CH3
+CH3O– Na+
CH3OH ?
heat
A)
O
B)
O
C)
O
D)
O
E)
O
Page 7
7.
What major product would you expect from the following reaction?
O
Na+ –OCH3
CH3OH, heat
?
CH2=O
A)
HO OCH3
B)
CH2
C)
O
CH3
D)
CH2
O
E)
O
Page 8
8.
Which proton in the following molecule is the most acidic?
CH2CH2C
O
H
H
H
2
5
4
3
1
A)
1
B)
2
C)
3
D)
4
E)
5
9.
What product is formed in the aldol condensation of propanal?
CH3CH2CHO KOH
H2O
?
A)
CHO
O
B)
CHO
OH
C)
OH
O
D)
HO CHO
E)
CHO
OH
Page 9
10.
To which side, if any, would the following equilibrium lie?
H3CC
O
CH3
H3CC
OH
CH2
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.
11.
To which side, if any, would the following equilibrium lie?
H3CC
O
CH3
H3CC
O
CH2
+ H2O
– Na+
+ NaOH
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.
Page 10
12.
Which major product would you expect when the following diketone undergoes aldol
cyclization in base, followed by acid?
O O NaOCH2CH3H3O+
A)
O
H3C
B)
O
O
C)
CH3
O
CH3
D)
O
CH3
E)
CH3
O
Page 11
13.
Which set of reagents would be needed for the following conversion?
O
CH3
O
CH3
CH2Ph
A)
NaOCH2CH3, CH3I
B)
PhCH2MgBr, then H3O+
C)
CH3MgBr, then PhCH2Br
D)
H3O+, then PhCH2Br
E)
LDA, then PhCH2Br
14.
What product results when the following aldol product is treated with dilute acid?
HO H
O
PhCH2
Ph
?
H3O+
A)
H
O
PhCH2
Ph
B)
H
OCH2H
O
CH2
Ph
Ph
+
C)
H
O
Ph
Ph
D)
O
H
OH
PhCH2
Ph
H
E)
None of these are formed.
Page 12
15.
Which of the following sets of reaction conditions will result in the following
transformation?
OOH
?
A)
1) PhMgBr / THF
2) H3O+
3) LAH / THF
B)
1) PhMgBr / THF
2) H3O+
3) LDA / THF
C)
1) PhMgBr / THF
2) H3O+
3) LAH / H2O
D)
1) (Ph)2CuLi
2) H3O+
3) NaBH4 / CH3OH
E)
1) (Ph)2CuLi
2) H3O+
3) MCPBA
Page 13
16.
Predict the major organic product of the following reaction.
CHO +O
NaOH / H2O
Heat ?
A)
OH O
B)
O
C)
O
D)
OOH
E)
Page 14
17.
Predict the major organic product of the following reaction.
O
+
O NaOEt / EtOH ?
A)
O
B)
O
C)
O
OH
D)
O
E)
O
Page 15
18.
Predict the major organic product of the following reaction sequence.
CH3O
O1) LDA / THF
EtO OEt
O
2)
3) LDA / THF
4) CH3CH2OTs
5) Saponification
6) H2O / H+
7) Heat
?
A)
CH3O
O
B)
CH3O
O
C)
CH3O
O
O
O
D)
CH3O
O
O
OEt
E)
CH3O
Page 16
19.
Predict the major organic product of the following reaction sequence.
O1) LDA (0.95 eq) / THF
2) CH3OTs
3) MCPBA
?
A)
O
O
B)
O
O
C)
D)
O
E)
O
O
H3C
Page 17
20.
The addition of either the methyl Grignard reagent or methyllithium to camphor,
followed by hydrolysis, produces a tertiary alcohol known as 2-methylisoborneol, an
algal metabolite which imparts a musty odor to water at very low concentrations.
However, the yield of alcohol does not exceed 50%, and large amounts of camphor are
recovered from the reaction even when a large excess of the Grignard or lithium reagent
are used. What would be the most plausible explanation?
O
camphor
1. CH3MgBr
or CH3Li
2. H2OOH
CH3
~ 50%
+ ~ 50%
unreacted camphor
A)
Ketones do not react with Grignard or lithium reagents.
B)
The Grignard or lithium reagent had obviously degraded during storage.
C)
The mechanism requires that, for each alcohol formed, one ketone molecule must
remain unreacted.
D)
With hindered ketones, the organometallic reagent could function as a base rather
than as a nucleophile.
E)
Alcohol formed early in the reaction could form an unreactive hemiacetal with
remaining ketone.
Page 18
21.
Predict the product of the following reaction:
OCl2, H
A)
O
Cl
B)
HO CH3
C)
Cl OH
D)
Cl
O
E)
Page 19
22.
One product of the following reaction would be:
CHO H
O
KOH/
A)
H
OO
B)
H
OH
C)
H CHO
D)
H
O
E)
None of these are correct.
23.
Which of the following conditions will not successfully alkylate a ketone?
A)
1. H2O, H+
2. CH3CH2OH
B)
1.
2. CH3CH2Br
3. H+, H2O
C)
1. LDA, THF
2. BrCH2CO2C2H5
D)
1. LDA, THF
2. (CH3)2C=CHCH2Br
E)
All of these will alkylate a ketone.
Page 20
24.
Predict the product of the following reaction:
O
1. nBuLi
2. H, H2O
A)
HO
B)
OH
C)
O
D)
OH
E)
O
Page 21
25.
Predict the product of the following reaction:
O1. (CH3CH2CH2CH2)2CuLi
2. CH3CH2I
A)
CH2CH3
(CH2)3CH3
B)
(CH2)3CH3
(CH2)3CH3
O
C)
CH2CH3
(CH2)3CH3
O
D)
CH2CH3
(CH2)3CH3
O
E)
CH2CH3
(CH2)3CH3
HO
Page 22
26.
Predict the product of the following reaction:
A)
B)
C)
D)
E)
No reaction occurs.
Page 23
27.
Predict the product of the following reaction:
A)
B)
C)
D)
E)
both B and C
Page 24
28.
Predict the product of the following reaction:
CH3NH2, H2O
O
A)
OH
NHCH3
NHCH3
B)
O
OH
C)
O
NHCH3
D)
O
NHCH3
NHCH3
E)
Page 25
NCH3
H
29.
Given a large excess of D2O, what product(s) would result from the following reaction
at equilibrium?
O
D2O
D+ or –OD ?
A)
D
OD
B)
O
D
D
D
C)
CD3
D3CCD3
O
DD
D
D
D
DD
DD
D)
O
D
D
D
E)
Both B and D would be formed.
Page 26
30.
The best reactants to convert cyclohexanone to 2-methylcyclohexanone cleanly would
be:
O O
CH3
?
A)
N H
2. CH3I
3. H3O+
1. , H+, – H2O
B)
NaOH, CH3I
C)
1. LDA
2. CH3I
D)
1. CH3Li
2. H3O+
E)
1. NaH
2. CH3I
3. H3O+
Page 27
31.
What would be the major product of the following reaction?
O
O
?
cat. NaOH
H2O
heat
A)
O
B)
O
C)
O
D)
O
OH
E)
O
OH
Page 28
32.
Which statement is true of the following reactions?
RCHO RCH
OH
OCH3
RCH
OCH3
OCH3
reaction IIreaction I
CH3OHCH3OH
A)
Reactions I and II are only acid-catalyzed.
B)
Reaction I is catalyzed by either acid or base, but reaction II requires acid.
C)
Reactions I and II are both base-catalyzed.
D)
Reaction II is catalyzed by either acid or base, but reaction I requires acid.
E)
Both reactions I and II are catalyzed by either acid or base.
Page 29
Answer Key