Sample problems for Exam 3
1. What is the IUPAC name of the compound shown hear?
O
H2N
COCH2CH3
A. p-aminophenyl ethanoate
C. ethylaniline enhydride
benz ocai ne
B. Ethyl p-aminobenzoate
D. ethanoic p-aminobenzamide
2. What is the correct structure for phenylbenzoate?
O
O
a.
C
b.
O
H3C
C
O
O
c.
C
O
O
CH3
d.
CH2O
C
CH2
3. IUPAC Name
O
N
A. N,N-diisopropylisobutanamide
B. N,N-diisopropyl-3-methylbutanone
C. N,N-diisopropyl-3-methylbutanamide D. Diisopropylisobutylamide
4. This reaction is an example of
A. Fischer esterification
D. Sandmeyer Reaction
B. Diels-Alder reaction
C. Aldal condensation
5. The reaction shown in Q.4 is an example of
a.
b.
c.
d.
nucleophilic acyl addition
nucleophilic acyl substitution
nucleophilic acyl elimination
nucleophilic acyl rearrangement
6. Cyclic esters are known as
a.
b.
c.
d.
a lactones
anhydrides
lactams
ethers
7. What is the major product in the reaction shown bellow?
O
O
1. LiAlH4, ether
2. H3O+
CH3
OH
OH
O
OH
OH
O
CH3
O
COOH
COOH
OH
C
B
A
H3C
B
8. What is the reactant in the following reaction?
O
(CH3CH2)2CuLi
ether, -78o
O
H
A
OCH3
OH
Cl
B
O
O
O
C
D
9. What is the major product in the reaction?
H
N
O
1. LiAlH4, ether
2. H3O+
H
N
H
H
N
HN
H
N
O
CH2
OH
B
A
D
C
10. Alpha- bromination of carboxylic acid by a mixture of Br2 and PBr3 is called
A. Hell-Volhard Zelinskii (HVZ) reaction
C. Robinson anuulation
B. Claisen- condensation reaction
D. Michael reaction
11. What is the major product in the following reaction?
Br
OH
Br
O
A
OH
OH
Br
Br
P
O
B
Br
C
D
12. What is the reactant in the reaction shown bellow?
2 equi NaOEt, EtOH
COOEt
COOEt
Br
Br
EtOOC
COOEt
EtOOC
COOEt
HO
A
OH
D
C
B
13. What is the appropriate reagent for the following reaction?
O
O
A. 1. Cl2/light, 2. KOH/EtOH
B. 1. Br2, CH3COOH, 2. Pyridine, Heat
C.1.BH3,THF, 2. H2O2, OH-
D. non
14. Which of the following is an example of diazonium ion?
A. CH3+N3-
B. CH3N2+
C. H2N – NH3+
D. none of these
15. The reaction of carboxylic derivatives by an organometallic reagent to yield
an alcohol is called
A. alcoholysis
B. Hydrolysis
C. Grignard reaction
D. reduction
16. Lactones are common names for
A. polyaromatic compounds
C. cyclic esters
B. cyclic ethers
D. cyclic amides
17. Which of the following is not considered to be a carboxylic acid derivatives?
A. acid anhydride
B. acid halide
C. amide
D. alkylhalide
18. Which one of the following compounds can not under go Aldol condensation?
H3C
CH3
O
C
C
H
H3C
CH3
O
C
C
CH3
H3 C
CH3
O
C
C
CH3
CH3
CH3
A
B
C
C2 H5
H3C
CH3
O
C
C
CH2Cl
CH3
D
19. This reaction is an example of:
O
O
O
H
H
a.
b.
c.
d.
H
NaOEt
EtOH
+ H2O
an intramolecular Claisen condensation
an intramolecular aldol condensation
a Robinson annulation
a Michael reaction
20. In the following reaction which carbonyl compound acts as a nucleophile?
O
O
O
H
CH2OH
5% NaOCH3, CH3OH
H +
A
A. A
B
B. B
C
C.C
D. none
21. The above reaction is an example of
a.
b.
c.
d.
a mixed Claisen condensation.
a Dieckman condensation.
a Michael reaction.
a mixed aldol reaction.
22. Acetoacetic ester can be prepared from ethyl acetate by the following
reaction.
O
O
1. NaOEt, EtOH
2. H3O+
C
H3C
OCH2CH3
This reaction is an example of
A. Aldol reaction
B. Claisen
O
C
H3C
C
CH2
OCH2CH3
C. Micheal reaction D. Dickmann reaction
23. The following reaction is an example of
O
O
O
OEt
O
1. NaOEt, EtOH
+ H3C
OEt
A. Dickmann cyclization `
C. Mixed Claisen reaction
OEt
2. H3O+
B. Mixed Aldol reaction
D. Robinson annulation
24. This reaction is known as
O
O
OEt
EtO
O
NaOEt
OEt
O
A. Intramolecular Claisen reaction
C. Robinson annulation
EtOH
B. Dickmann cycization
D. A & B
25. The structure shown bellow is a product of Michale reaction.
O
O
O
Identify the Michael donor and Michael acceptor from the compounds bellow
O
O
O
O
A. 1 & 2
4
3
2
1
O
O
B. 2&3
C. 1 & 4
D. 2 & 4
26. The following is an example of
NH
O
HN
+
O
A. Claisen condensation
D. Diels-Alder reaction
B. Michael reaction
C. Stork reaction
27. What are the products in the following Robinson annulation reaction?
O
O
CH3
+
H2C
CH
C
CH3
NaOEt, EtOH
O
Michael adduct
NaOEt, EtOH
heat
Robinson annulation product
O
O
O
A.
CH2CH2CCH3
and
CH3
O
O
O
O
O
O
B
CH2CH2CCH3
and
CH3
O
O
O
O
C
and
CH2CH2CCH3
O
CH3
D. None of the above
28. Rank the following compounds in order of increasing basicity. Label the least
basic compound “1” and the most basic compound “4”. Place the number
corresponding to the compound’s rank in the blank below the compound.
NH2
H3C
NH2
CH2NH2
NH2
CH3
CF3
29. The following reaction is known as
O
O
N
H
OH
Br2
NaOH, H2O
NH2
O
a.
b.
c.
d.
a Curtius rearrangement
a Hofmann elimination reaction
a Gabriel synthesis
a Hofmann rearrangement
30. In the following reaction the intermediate A is
CH3NH2
H2/Ni
NCH3
O
A
a.
b.
c.
d.
an imine
an enamine
an iminium ion
an imide
NHCH3