FIRST REVIEW EXAM
1.
ORGANIC CHEMISTRY 2220, SPRING 2001
What splitting pattern will be observed for the underlined hydrogen in a proton NMR
spectrum of the following compound?
O
C
A. singlet
2
H
B. doublet
C. triplet
D. quartet
An unknown having the molecular formula C8 H8 O gave the following proton NMR
spectrum:
singlet, d 9.91 , 1 H
doublet, d 7.80, 2 H
doublet, d 7.30, 2 H
singlet, d 2.20, 3 H
What is the structure of this unknown?
CH3
O
A. CH3
CH
O
B.
CH
O
CH
CH3
D. HO
C.
CH3
3.
Which of the following is the best synthesis of hexane from propyl bromide?
(CH3CH2)2CuLi
A.
ether
C.
CH3CH2CH2MgBr
ether
Li
CuI
CH3CH2CH2Br
ether
B. ether
ether
Mg
D.
ether
CH3CH2CH2Br
ether
H+/H2O
*A*
4.
What are the necessary reagents and conditions to carry out the following transformation?
A.
5.
CH2OH
NaBH4, H2O
D.
PCC
CH2Cl2
(2E,4E,6E)-3,4-dimethyl-2,4,6-octatriene
(2Z,4Z,6E)-3,4-dimethyl-2,4,6-octatriene
(2E,4E,6Z)-3,4-dimethyl-2,4,6-octatriene
(2Z,4Z,6Z)-3,4-dimethyl-2,4,6-octatriene
What will be the total number of rings in the Diels-Alder product obtained from an acyclic
diene and an acyclic dienophile?
A. 0
7.
B.
CH3O C
What is the name of the triene below?
A.
B.
C.
D.
6.
H+/H2O
CrO3/H2SO4
C.
?
CH
CH3O C
LiAlH4
ether
O
O
O
B. 1
C. 2
D. 3
How many signals are there in the proton magnetic resonance spectrum of the compound
shown?
CH3
CH3
H
H
A. 2
B. 3
C. 4
D. 5
8.
What is the major organic product, B, of the reaction sequence shown?
CH3 -C-CH3 + LiAlD4
||
O
9.
10.
--------------> A
H2 O
-------------> B
A. CH3 -CH-CH 3
|
OD
B. CH3 -CD-CH 3
|
OD
C. CH3 -C-CH2 D
||
O
D. CH 3 -CD-CH 3
|
OH
Which of the following compounds has an absorption maximum above 200 nm in its
UV-Vis spectrum?
CH 2
A.
CH3 CH
CH-CH
B.
CH 2
CH-CH 2 CH
C.
HC
C-CH 2 CH2 CH2 CH3
D.
CH3 CH2 CH 2 CH2 CH2 CH3
CH2
What is the major organic product of the reaction shown?
+
Br 2
low temperature
?
CCl 4
Br
A.
B.
Br
Br
11.
C.
Br
D.
Br Br
How many signals are present in the 13 C NMR spectrum of the following compound?
CH2 CH3
A. 5
B. 6
C. 7
D. 8
12.
What is the major product of this reaction?
Br
H3C
+ (CH3)2CuLi
Br
H3C
CH3
CH3
H3C
B.
A.
13.
CH2CH3
H3C
D. CH3CH2CH2Br
C.
What is the product of the reaction?
O
O
H3C CC H2 CH 2CO H
OH
H
+
NaBH4
OH
O
O
OH
O
H
A. H3C CC H2C H 2COH B. H3C CC H2 CH 2COH C.H 3C CC H 2C H2 COH D. H3C CC H2 CH 2 COH
H
14.
H
H
H
Which of the following dienes is MOST stable?
A.
C.
15.
H
CH=CHCH3
CH=CHCH3
CH=CHCH3
B.
CH 2
D.
Which of the following reacts fastest with maleic anhydride in a Diels-Alder reaction?
CH3
CH2
A.
B.
C.
CH3
CH3
D.
CH2
16.
In the following molecule, which of the indicated protons gives a signal with the highest δ
value (most deshielded)?
COOH
D
CHCHO
B
C
A
17.
What is the major organic product of the reaction sequence shown?
H3 O +
C6 H5 Li + C6 H5 COOCH2 CH3
OH
OH
B C6 H5 CHCH 2 CH3
A C6 H5 CHC6 H5
O
D. C 6 H5 CC6 H5
C. ( C 6 H5 )3 COH
18.
Which of the following compounds does not react with CrO3 /H2 SO 4 ?
A.
OH
B.
C.
H
D.
OH
O
O
19.
Which of these is the most stable cation?
A.
+
B.
C.
+
D.
+
+
20.
What is the product of the following Diels-Alder reaction?
+
CO2CH3
?
CO 2 CH3
CO 2C H3
A.
B.
C.
CO 2C H3
D.
CO 2 CH3
21.
Electromagnetic radiation having a long wavelength has a _____ energy and a _____
frequency.
A.
B.
C.
D.
22.
high . . . high
high . . . low
low . . . high
low . . . low
Which of the following compounds corresponds to the given NMR data?
doublet, δ 1.11, 6H
singlet, δ 2.14, 3Η
septet, δ 2.58, 1Η
A.
O
B.
O
O
O
C.
D.
H
23.
What reagent would you use to carry out the following reaction?
O
A. NaBH4
OH
H
B. CrO3 , H2 SO 4
C. pyridinium chlorochromate (PCC)
D. KMnO4
24.
Which of the following compounds a) does not react with CrO3 /H2 SO 4 and b) is insoluble
in sulfuric acid?
A.
O
OH
O
B.
C.
D.
H
25.
Which of the following compounds is NOT a conjugated diene?
A.
B.
C.
D.