Page 1
1.
Rank the following carboxylic acid derivatives in order of decreasing reactivity toward
hydrolysis (most reactive on left):
H3CC
O
Cl H3CC
O
OCH3H3CC
O
NH2
H3CC
O
OCH3
C
O
A B C D
A)
D > B > A > C
B)
C > A > B > D
C)
B > D > A > C
D)
A > B > D > C
E)
D > B > C > A
2.
Which of the following is not an intermediate in the Hofmann rearrangement of
ethanamide to methylamine?
H3C C
O
NH2CH3NH2
Br2
NaOH
H2O
A)
H3C C
O
NH
–
B)
C)
H2C C
O
NH2
–
D)
O
H
OH
H3C
N C
E)
H3C C
O
NHBr
Page 2
3.
In the reaction shown below, which product(s) would be formed?
H3CCH2C
O
OH ?
H+
heat
+ CH318
OH
A)
H3CCH2C
O
OCH3
18
B)
H3CCH2C
O
OCH3
18
C)
H3CCH2C
O
OCH3
18
18
D)
H3CCH2C
O
OH
16
16
E)
both A and B
Page 3
4.
Which of the following would be properly named as 2-chloroethyl benzoate?
A)
CH2CH3
C
O
O
Cl
B)
CH CH3
C
O
O
Cl
C)
CH2CH3
C
O
O
Cl
D)
CH2CH3
C
O
O
Cl
E)
CH2CH2Cl
C
O
O
5.
Which reagent(s) would accomplish the following transformation?
H3CCH2C
O
Cl H3CCH2C
O
CH3
?
A)
CH3Li
B)
CH3I, NaOH
C)
CH3MgBr
D)
(CH3)2CuLi
E)
either A or C
Page 4
6.
How many different CH3 signals would you expect in the room-temperature proton
NMR spectrum of the molecule below?
H3C C
O
N(CH3)2
A)
One
B)
Two
C)
Three
D)
Four
E)
Five
7.
What would be the name of the following cyclic ester?
O
O
H3C
A)
-valerolactone
B)
-butyrolactone
C)
2-methyl--butyrolactone
D)
2-methyl--butyrolactone
E)
2-methyl--valerolactone
8.
What would account for the fact that the molecule below racemizes easily, despite
having three chiral centers?
O
O
H
H
HOH2C
A)
Lactones are configurationally unstable
B)
Molecule loses CO2 easily
C)
Enolization occurs easily
D)
Intramolecular transesterification occurs easily
E)
This molecule is not chiral.
Page 5
9.
What would be the major organic product of the following reaction?
C
O
NH2?
1. LiAlH4
2. H2O
A)
CH2OH
B)
CH2NH2
C)
C
O
H
D)
C
O
OH
E)
CH3
10.
What type of functional group do the natural products known as waxes have?
A)
Ester
B)
Amide
C)
Carboxylic acid
D)
Alcohol
E)
Amine
Page 6
11.
What would be the major organic product expected from the following reaction?
CH3C
O
OCH2CH3?
1. CH3MgBr (xs)
2. H2O
A)
CH3C
O
CH3
B)
CH3C
OH
CH2CH3
CH3
C)
CH3C
OH
OCH2CH3
CH3
D)
CH3C
CH3
CH3
OH
E)
CH3C
OH
CH2CH3
CH2CH3
12.
What would be the product of the following reaction?
?
C6H5CH2Br 1. NaCN
2. H3O+, heat
A)
C6H5CO2H
B)
C6H5CH2CO2H
C)
C6H5CH2OH
D)
C6H5CH2CH2NH2
E)
C6H5CH3
Page 7
13.
What would be the proper name of the following?
NO2
C
O
OCH3
A)
3-nitro-methylbenzoate
B)
methyl 3-nitrobenzoate
C)
3-nitro-methoxybenzoate
D)
5-nitro-methylbenzoate
E)
3-nitrocarboxymethylbenzene
14.
What would be the organic product of the following reaction?
(CH3)2CHCOCl + (CH
3)2CuLi H2O?
A)
H3CCH
CH3
C
O
CH3
B)
H3CCH
CH3
C
O
OCH3
C)
H3CCH
CH3
C
OH
CH3
CH3
D)
H3CCH
CH3
C
OCH3
CH3
CH3
E)
None of these.
Page 8
15.
Lactones are:
A)
Cyclic amides
B)
Cyclic anhydrides
C)
Cyclic esters
D)
Cyclic acids
E)
Cyclic ketones
16.
What would be the organic product of the following reaction? (18O is a rare oxygen
isotope.)
COCH3
O
?
H+
+ CH3CH 2OH
18
A)
COCH2CH3
O
+ CH3OH
18
B)
COCH2CH3
O
+ CH3OH
18
C)
COCH2CH3
O
18
CH3OH
+
D)
More than one of these.
E)
None of these.
Page 9
17.
What would be the organic product of the following reaction?
CH3
OH
OH
O
(-)-menthol
+H+
?
A)
CH3
O
O
B)
CH3
O
O
C)
mixture of A and B
D)
None of these.
E)
No reaction occurs.
18.
Which of the reactions listed below would produce benzyl acetate (= benzyl ethanoate)?
A)
(CH3CO)2O
C6H5CH2OH pyridine
B)
CH3CO2H
C6H5CH2OH H+, – H2O
C)
CH3COCl
C6H5CH2OH pyridine
D)
two of these
E)
all of these
Page 10
19.
The product of the following reaction would be:
O
O
O
+ CH3CH2OH ?
A)
CO2CH2CH3
CO2CH2CH3
B)
CO2H
CO2H
C)
CO2H
CO2CH2CH3
D)
O
HO
O
OCH2CH3
E)
H
C
O
C
O O
OCH2CH3
Page 11
20.
What would be the major expected product from the reaction shown below?
C
O
OCH3
1. PhMgBr
(excess)
2. H2O
?
A)
C
O
B)
C
OH
CH3
H
C)
C
OH
H
D)
C
OH
E)
C
OH
CH3
Page 12
21.
Substitutions at sp2 carbons do not occur by an SN2 mechanism, but rather by way of a
“tetrahedral intermediate.” The tetrahedral intermediate shown could occur in which
reaction?
CH3CH2C OCH3
OH
NH2
A)
methyl propanoate + ammonia
B)
propanamide + hydroxide
C)
propanoic acid + methanol
D)
propanamide + ethanol
E)
None of these.
22.
What would be the product of the following reaction?
CH3C
O
OCH2CH2
CH2C
O
OCH2CH3?
H3O+
heat
A)
H2C
H2CCH2
O
O
+ CH3CO2H + CH
3CH2OH
B)
OCH2CH2
CH2C
O
OH
C
O
CH3+ CH3CH2OH
C)
HO CH2CH2
CH2C
O
OCH2CH3+ CH3CO2H
D)
CH3CH2
CH2C
O
OH + CH3CO2H + CH3CH2OH
E)
None of these.
Page 13
23.
A multistep preparation of propylpropanoate from only 1-propanol would require the
use of how many of the reagents below (i.e., what reagents would you need to use if you
only had 1-propanol to start with)?
CH3CH2CO2CH2CH2CH3
NaCN
H+
1. Mg, ether
2. CO2
3. H3O+H2CrO4
H3O+
– H2O
A)
Two of the above.
B)
Three of the above.
C)
Four of the above.
D)
All of the above.
E)
The preparation cannot be done with only these reagents.
24.
What would be the products of the following reaction?
CH3CH2CH2CO2CH3 + CH3NH2?
A)
CH3CH2CH2CH2NH(CH3) + H2O
B)
CH3NHC(=O)CH2CH2CH3 + CH3OH
C)
CH3CH2CH2CONH2 + CH3CH2OH
D)
CH3OH + CH3CH2CH2OC(=O)NHCH3
E)
CH3CH2CH2NH(CH3)COCH3 + H2O
25.
How can the importance of the following resonance be evaluated?
R C
O
NH2R C
O
NH2
–+
A)
Charged resonance structures are always more important.
B)
The C=O IR stretch for amides is significantly different than for other C=O groups.
C)
The water solubility of amides implicates charged structures.
D)
The C-N rotational barrier can be determined by NMR.
E)
More than one of the above are correct.
Page 14
26.
What is the relative reactivity of carboxylic acid derivatives toward hydrolysis (left =
least reactive)?
A)
ester < amide < acid chloride < anhydride
B)
amide < ester < acid chloride < anhydride
C)
ester < amide < anhydride < acid chloride
D)
amide < ester < anhydride < acid chloride
E)
The relative reactivities really cannot be compared.
27.
When compound X is heated with aqueous acid, acetic acid and acetaldehyde (ethanal)
are formed. The proton NMR spectrum of X is shown below. What is the structure of
X?
A)
CH2=CHO2CCH3
B)
CH2=CHOCH2CH3
C)
CH2=C(CH3)O2CH
D)
CH3CH=CHO2CH
E)
CH2=CHCH2CO2H
Page 15
28.
What would be the other product of the following reaction?
? + HOCH
2CH3
1. CH3MgBr
2. H3O+
C6H5CO2CH2CH3
A)
CH3
OH
CH3
B)
CH3
O
C)
OH
O
D)
CH3
O
O
E)
CH3
O
29.
Which of the following has the highest IR absorption frequency for the C=O group?
R C R
O
R C OR
O
R C NH2
O
R C H
O
R C Cl
O
54321
A)
1
B)
2
C)
3
D)
4
E)
5
Page 16
30.
4-Hydroxybutanoic acid spontaneously cyclizes to give what compound?
A)
O
O
B)
O
O O
C)
O
O
O
D)
OO
E)
O
OH
H
31.
Reduction of which of the following esters with lithium aluminum hydride would yield
two molecules of the same alcohol?
A)
O
O
B)
O
O
C)
O
O
D)
O
O
E)
None of these.
Page 17
32.
What reagent(s) would be required to achieve the following conversion?
C
O
OH C
O
H
?
A)
1. SOCl2, ?
2. LiAl(OtBu)3H
B)
1. NaBH4
2. H2CrO4
C)
1. LiAlH4
2. H2O
3. PCC
D)
1. Br2, cat. P
2. H2O
E)
both A and C
33.
Which of the following would be most likely to result from saponification of a natural
triglyceride?
triglyceride NaOH
H2O
?
A)
Na+ – OC
O
B)
Na+ – OC
O
C)
Na+ – OC
O
D)
Na+ – OC
O
E)
Na+ – OC
O
Page 18
34.
Place the following compounds in order of increasing rate of hydrolysis.
O
O O
Cl
OO
ON
O
III III IV
A)
I, III, IV, II
B)
IV, II, III, I
C)
III, I, II, IV
D)
I, II, IV, III
E)
All carboxylic derivatives exhibit similar reactivities with H2O.
35.
What is the product of combining pentanoic acid with thionyl chloride, followed by
propanol and base?
A)
pentanol
B)
pentyl propanoate
C)
propyl pentanoate
D)
1-tosyl pentanol
E)
1-chloropentanol
36.
Predict the product of the following reaction:
O
O
NH2
+
A)
N
B)
N
C)
ON
D)
N
O
E)
None of these.
Page 19
37.
Predict the product of the following reaction:
Br
O
H2O
A)
OH
O
B)
H
O
OH
C)
H
HO OH
D)
H
O
E)
no reaction occurs
38.
Which of the following is a lactam?
A)
N
O
B)
N
O O
H
C)
N
O
D)
OH
O
E)
Two of these can be considered lactams.
Page 20
39.
Predict the product of the following reaction:
NH2
O
Br2, NaOH, H2O
A)
OH
O
B)
NH2
HO
C)
NH2
OH
D)
NH2
+
COO
E)
NH3
Page 21
40.
What structure is not an intermediate in the following reaction?
A)
B)
C)
D)
E)
None of the above.
Page 22
41.
Which of the following reactions will produce N-methyl benzamide?
A)
B)
C)
D)
both A and C
E)
All of the above.
Page 23
42.
Which of the following reactions will not give a carboxylic acid as a product?
A)
B)
C)
D)
E)
Page 24
43.
What is the product from the following reaction?
A)
B)
C)
D)
E)
44.
What reagent is needed to complete the reaction shown?
CH3CH2C
CH3CH2C
O
Cl
O
CH
CH3
CH3
?
A)
((CH3)2CH)2CuLi
B)
KCN/NaOH
C)
HOCH(CH3)2
D)
BrMgCH(CH3)2
E)
(CH3)2CHLi
Page 25
45.
Which, if any, functional group in the molecule below would undergo basic hydrolysis
most easily?
O
N
C
H3C
O
CN
O
H
A
B
C
D
A)
A
B)
B
C)
C
D)
D
E)
None of these groups would react.
46.
Which functional group has the lowest IR absorption frequency?
A)
RC
O
H
B)
RC
O
R
C)
RC
O
OR
D)
RC
O
NR2
E)
R C N
Page 26
Answer Key
Page 27