CH221 ORGANIC CHEMISTRY I
QUIZ 4
11 MAY 2008
Time allowed: 80 minutes
Attempt all 40 questions by writing answers for each question on the grid answer sheet provided
1.
Which of the circled C-H bonds has the lowest bond
8.
What is the reagent for the following reaction?
9.
Which of the following compounds is (are) a tautomer of
dissociation energy?
compound X drawn below?
2.
Determine the product.
3.
Determine the product
A.
Compound A
B.
Compound B
C.
Compound C
D. Compounds A and B are both tautomers of compound X.
4.
E.
Determine the product.
10.
Compounds A, B, and C are all tautomers of compound X.
Which method would work the best in carrying out the
following conversion?
5.
Determine the product(s).
A.
6.
Determine the product.
(1) HBr; (2) 2 NaNH2
B.
(1) Br2; (2) 2 NaNH2
C.
(1) Br2, H2O; (2) NaNH2
D. (1) BH3, THF; (2) H2O2, NaOH; (3) NaNH2
E.
11.
(1) NaNH2
Give the IUPAC name for the following compound.
CH3C(CH3)2CH2C
7.
CCH2CH(CH2CH2CH3)CH3
Determine the product.
12. Draw a product(s) of the following reaction.
1
13.
14.
Determine the product.
22.
What is the reagent in the reaction below?
23.
Ozonolysis of compound a below would yield which
Determine the product.
product(s)?
15.
Determine the product.
16.
Determine the product.
A. A
17.
Determine the reagent.
B.
B
C.
C
D. D
E.
Products A and B
24. When a compound A with molecular formula C12H16 is treated
18.
Determine the reagent.
with excess H2 in the presence of Pd, a compound having
molecular formula C12H20 is formed. How many rings and
double bonds does compound A possess?
19.
Determine the reagent.
A. Compound A has no rings and 5 double bonds.
B.
Compound A has 1 ring and 4 double bonds.
C.
Compound A has 2 rings and 3 double bonds.
D. It's impossible to tell how many rings and double bonds are
present.
E.
None of the statements are correct.
20. After ozonolysis and treatment of the ozonide with zinc,
compound A was converted to the compound below. What is the
structure of compound A?
21.
What is the starting material in the reaction below?
2
25. The organic starting material undergoes reduction in all of the
following reactions except one. In which reaction is the organic
substrate not reduced?
30.
What type(s) of molecular motion is (are) observed using
infrared spectroscopy?
A.
Stretching and bending
B.
Rotation and excitation
C.
Spin flipping
D. Fragmentation
31.
The functional group region of an infrared spectrum is
A.
26. Determine the product.
where the cations appear.
B.
>1500 cm-1.
C.
<1500 cm-1.
D. >2500 cm-1.
32.
Why is the infrared absorption for the stretching motion of
internal alkynes rarely observed?
27. Fill the boxes in the following synthesis.
A.
They do not form cations.
B.
They are too strong.
C.
There must be a change in dipole.
D. They don't have hydrogens.
33. Stronger bonds will be found where in the infrared spectrum?
A.
Higher molecular weight
B.
Lower molecular weight
C.
Lower wavenumbers
D. Higher wavenumbers
34.
Consider the three organic compounds drawn below. Which of
the following statements is (are) true about the IR spectra of
28. Rank the following compounds in order of increasing
oxidation level (from lowest to highest).
compounds A, B, and C?
29. In conventional mass spectrometry, what is being detected?
A.
The molecular weight of the compound
B.
The molecular formula of the compound
C.
The mass of any cationic species
D. The mass of any neutral species
A.
Compound A shows strong absorptions at 3000 cm-1 and
1700 cm-1.
B.
Compound B shows strong absorptions at 3000 cm-1 and
2250 cm-1.
3
C.
Compound C shows strong absorptions at 3000 cm-1 and
C.
3200-3600 cm-1.
Because a small percentage of the compound will have a
carbon that is the isotope 13C instead of 12C
D. Statements (Compound A shows strong absorptions at
D. Because of fragmentation
3000 cm-1 and 1700 cm-1) and (Compound C shows
strong absorptions at 300 cm-1 and 3200-3600 cm-1) are
39.
Examine the IR below and classify the compound.
true.
E.
Statements (Compound A shows strong absorptions at
3000 cm-1 and 1700 cm-1), (Compound B shows strong
absorptions at 3000 cm-1 and 2250 cm-1), and (Compound
C shows strong absorptions at 3000 cm-1 and 3200-3600
cm-1) are all true.
35. Which of the circled C-H bonds absorbs at the highest wave
number in the IR spectrum?
36.
A.
Alcohol
B.
Aldehyde
C.
Amine
A compound X shows a molecular ion at 72 in its mass
D. Ketone
spectrum, and a strong peak at ~1700 cm-1 in its IR spectrum.
E.
Acid
Which structures are possible for compound X?
40.
Examine the IR below and classify the compound.
37. Draw a structure that is consistent with a compound that
displays a molecular ion at 56 and infrared signals at 2250 and
3600-3200 cm-1?
38.
In a typical mass spectrum, a smaller signal is observed at a
A.
Alcohol
mass 1 amu higher than the molecular ion peak. Why?
B.
Aldehyde
C.
Amine
A.
B.
Due to small impurities in the sample
Machine error
D. Ketone
E.
Acid
4
CH221 QUIZ 4 ANSWER GRID
Name………………………..
Student Number………………………
1
2
B
3
4
O
5
6
Br
7
8
2HCl
O
Br
9
10
11
D
B
2,2,7-trimethyl-4-decyne
13
12
O
O
14
15
16
O
O
O
17
H
H3C
H3CH2C
OH
H
H3C
H3CH2C
H
CH3
18
H2, Lindlar catalyst
CH3
H
OH
19
20
K2Cr2O7
X
H2SO4, H2O /
CrO3, H2SO4, H2O
21
22
RCO3H,
,
H2O(OH-
23
24
25
E
E
D
H+)
26
27
A : CH3CH2Br
OH
H3CH2C
H
D:
B : CH3CH2C≡C-
O
H
CH3
C : Na, NH3
H3CH2C
H
O
H
CH3
28
29
30
31
32
BDCA
C
A
B
C
33
34
35
36
37
D
D
A
A
38
39
40
C
D
A
OH
Total
5