Final Exam
004:121
Organic I
Spring 2007
5/7/07
Final Exam Last Name ______________________ First Name ______________________ (PRINTED) (PRINTED) UI ID #
_________________________________
Write your name on each page. Please read each question carefully before answering. Answer the questions in ink in the spaces provided inside. If you make changes as you go, please make sure your final answer is clearly indicated. Total points = 200. You have 120 min. Good Luck! _______________________________________________________________________
Grading: Q.#
Score
(Max)
1.
__________ (72 pts)
2.
__________ (14 pts)
3.
__________ (11 pts)
4.
__________ (10 pts)
5.
__________ (12 pts)
6.
__________ (10 pts)
7.
__________ (14 pts)
8.
__________ (12 pts)
9.
__________ (15 pts)
10.
__________ (8 pts)
11.
__________ (6 pts)
12.
__________ (16 pts)
Total __________ (200)
Chem. 121
1.
Final Exam (5/7/07)
Name_____________________________________
(3 pts each) Please circle one answer for each question.
A. Which is the appropriate conversion from condensed formula to skeletal formula? (CH3)2ClCC(CH3)2COH(CH3)2 B.
A. Cl
OH
D. A and B
OH
C.
Cl
OH
Cl
E. All of the above
B. Indicate the hybridization of all of the second row elements in the following compound. A. B. C. D. E.
A-sp3; B-sp3; C-sp2; D-sp2; E-sp3 A-sp2; B-sp2; C-sp2; D-sp3; E-sp3 A-sp3; B-sp2; C-sp2; D-sp3; E-sp2 A-sp3; B-sp2; C-sp3; D-sp2; E-sp2 A-sp2; B-sp3; C-sp3; D-sp3; E-sp2
A
O
..
B
N
HN O
..
..
N H
D
..
N H
C
E
C.
Rank the following hydrogens (1, 2, and 3) in order of increasing acidity. 2 H A. 1, 2, 3 B. 2, 3, 1 C. 3, 2, 1 1 H D. 3, 1, 2 E. 2, 1, 3 3 H
D.
Which one of the following compounds has the highest boiling point? A. CH2 =CH(CH2 )4 CH3 B. CH3(CH2 )5 NH 2 C. CH3(CH2 )5 Cl D. (CH3 CH2 )3N E. CH3(CH2)5 Br
E.
Consider the molecule below, the nitrogen atom can best act as a A. electrophile .. B. nucleophile N C. base D. acid E. none of the above
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Chem. 121
F.
Final Exam (5/7/07)
Name_____________________________________
Give the IUPAC name for the following compound. A. 1,1-diethyl-4-methyl-cyclohexane B. cis-1,1-diethyl-4-methyl-cyclohexane C. trans-1,1-diethyl-4-methyl-cyclohexane D. 3-(4-methyl-cyclohexyl)-pentane E. 3-ethyl-3,6,-ethyl-heptane
G.
Designate the following stereogenic centers as R or S (left side first). A. B. C. D. E.
S,R. S,S. R,S. R,R. None of the above. CH3 H HO CH2OH
A
Consider the following pairs of molecules: H.
Which pair of molecules represents a pair of enantiomers? B
I.
J.
Which pair of molecules does not represent isomers?
H CH2OH H
HOH2C
CH3 H HO CH2OH
OH H HOH2C CH3
C
CH2OH H HO CH2OH
HOH2C
D
CH3 H HO CH2OH
OH CH3 HOH2C H
H CH2OH H
An achiral compound that contains tetrahedral stereogenic centers is called: A. a diastereomeric molecule B. an orto C. a tetrameric molecule D. a stereogenic molecule E. a meso
K.
Which of the following is a meso compound?
A
B
C
D Page 3
E %
Chem. 121
L.
Exam II (3/21/07)
What is the correct stereochemical assignment for each of the following alkenes?
F
F
A A. B. C D. E. M.
C
D
A = E; B = Z; C = E; D = Z A = Z; B = E; C = E; D = E A = E; B = E; C = Z; D = Z A = E; B = E; C = Z; D = E A = E; B = E; C = E; D = E
R,R-4-chloro-2-hydroxyl-2,3,3,4-tetramethyl-pentane S,R-4-chloro-2-hydroxyl-2,3,3,4-tetramethyl-pentane R,S-2-chloro-2,3,3,4-tetramethyl-pentanol 4-chloro-2,3,3,4-tetramethyl-2-pentanol R,R-4-chloro-2,3,3,4-tetramethyl-2-pentanol
Cl OH
Predict the two most likely mechanisms for the reaction of 3-iodopentane with potassium tertbutoxide in DMSO (an aprotic solvent). A. B. C. D. E.
O.
B
What is the IUPAC name of the following molecule? A. B. C. D. E.
N.
Name_____________________________________
SN2 and SN1 E1 and E2 SN2 and E2 E1 and SN1 E2 and SN1
When S-2-bromobutane undergoes an SN1 reaction with methanethiol (CH3SH), what configuration(s) is/are present in the product? A. S only B. R only C. 50%:50% mixture of R and S D. Meso E. None of the above
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Chem. 121
P.
OH
?
CH3
Br
H3C
NaH, CH3I PBr3, then CH3I CH3OH O3, CH3SCH3 A and C
The rate equation that describes the reaction shown below is: A. B. C. D. E.
T.
Br2, peroxides NaH, CH3CH2Br TsCl, then NaBr PBr3 C and D
A suitable method for converting 1-butanol to butyl methyl ether is: A. B. C. D E
S.
a C-H bond breaks a Br-H bond forms a C-Br bond forms a Br-Br breaks a C-C bond breaks
Which set of reaction conditions will provide the indicated product? A. B. C. D. E.
R.
Name_____________________________________
Which of the following does not occur in the propagation phase of free radical bromination of ethane to form bromoethane? A. B. C. D. E.
Q.
Exam II (3/21/07)
k[A] k[C][D] k[B] k[A][B] k([C][D]/[A][B])
Br +
A
NaOCH3
B
+
NaBr
C
D
The reaction between (CH3)3CI and CH3CH2OH to give (CH3)3COCH2CH3 is an example of: A. B. C. D. E.
S N2 S N1 Oxidation Addition E1 Page 5
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Chem. 121
U.
h!
Cl +
Cl2
2 3 4 5 6
How many propagation steps are required in the radical polymerization of venyl chloride to for the following PVC (poly-vinylchloride)? A. B. C. D. E.
X.
2 3 4 5 6
How many degrees of unsaturation are present in a compound with molecular formula C13H24? A. B. C. D. E.
W.
Name_____________________________________
How many products (including stereoisomers) would you expect to obtain upon mono-chlorination of the indicated substrate under the conditions shown? A. B. C. D. E.
V.
Exam II (3/21/07)
2 3 4 5 6
Cl RO
Cl
Cl
Cl OR
How many initiation steps are required in the radical polymerization of vinyl chloride to form the following PVC (poly-vinylchloride)? A. B. C. D. E.
2 3 4 5 6
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
2. A.
(8 pts) List the four main intermolecular forces between organic molecules from weak to strong.
1. __________________________________
2. __________________________________
3. __________________________________
4. __________________________________
B.
(6 pts) Ionophores selectively allow ions to cross biological membranes. List the three most important properties of the ionophore?
1. __________________________________
2. __________________________________
3. __________________________________
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
3. A. (2 pts) Circle all the nucleophilic atoms in the following molecule. B. (5 pts) Draw all the possible resonance structures for this molecule.
O -O
NH2
C. (4 pts) The Ka of acetone (2-propanone: CH3 COCH3) is 10-20 and the pKa of propane is 50. Which one is more acidic?
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
4. A. (6 pts) The following compound has another chair conformation. Which conformation is more stable? What is the distribution of these two conformers?
B. (4) Name this compound: __________________________________________________________ 5. A. B.
(2 pts) How many stereogenic centers does the following compound have? The specific rotation of the commercial drug l-Dopleron is [α] = -10˚*ml*g-1*dm-1. For a newly synthesized sample of Dopleron, the measured α was + 0.2˚ (1 dm cell), and the percentage of d- and of l-Dopleron was 55 % and 45%, respectively. 1. (4 pts) What is the ee in this sample?
2. (6 pts) What is the concentration of total Dopleron in this sample (show your calculations)?
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
6. A. (6 pts) Which of the following molecules contain a poor leaving group (circle all that apply)? 1. CH3CH2CH2CH2Cl
2. CH3CH2CH2OH
3. CH3CH2CH2OHZnCl2
4. CH3CH2CH2OTs
5. CH3CH2CH2OCH3
B. (4 pts) Complete the sentence: In ________________________ reactions, the stability of the product has little effect on the energy of the transition state. However, in _______________________ reactions it has substential effect on the energy of the transition state.
7. (14 pts) Supply the missing products and reagents. A
E O3, then (CH3)2S
NBS, h!
B
D
HBr
C
C
G
H2SO4, HgSO4 H2O
Br2
C
NaH, then CH3Br
F
A
E
B
F
C
G
D
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
8. Use the reaction coordinate diagram below to answer the following questions.
2
3
4
1 5
a) (2 pts) How many intermediates are there in the reaction?
b) (2 pts) How many endothermic steps are there in the reaction?
c) (2 pts) Is the overall reaction exothermic or endothermic?
d) (2 pts) Does transition state structure 2 more closely resemble 1 or 3?
e) (2 pts) What effect will increasing the rate of reaction for 1 going to 3 have on the rate of the overall reaction?
f) (2 pts) What kind of reaction mechanism is illustrated in the energy diagram?
Page 11
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Chem. 121
9.
Exam II (3/21/07)
Name_____________________________________
(15 pts) Draw only the main product of the following reactions: OTs
NaOC(CH3)3
1. CH3CH2ONa O
2. H2O
HBr
2 equiv HBr
KMnO4 H2 O
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
10. (8 pts) Draw the mechanism for the following rearrangement:
H2SO4
11.
(6 pts) In which steps of the radical polymerization of vinyl chloride to form PVC (poly-vinylchloride) were bonds A and B formed? A
B
Cl
A. ____________________________________
RO
Cl
Cl
Cl OR
B. ____________________________________
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
12. A. (10 pts) Synthesize 2-propene-1-ol from organic compounds with no more than two carbons (no limitations on other atoms, e.g., halides, oxygen, etc.). Draw all precursors (intermediates) and indicate the reagents used.
B. B. (6 pts) Use the 2-propene-1-ol (part A above) to synthesize S-3-methoxy-propane-1,2-diol in no more than three steps. Draw all precursors (intermediates) and indicate the reagents used. OH O
Page 14
OH
%
Organic I
Spring 2007
5/7/07
Final Exam Last Name ______________________ First Name ______________________ (PRINTED) (PRINTED) UI ID #
_________________________________
Write your name on each page. Please read each question carefully before answering. Answer the questions in ink in the spaces provided inside. If you make changes as you go, please make sure your final answer is clearly indicated. Total points = 200. You have 120 min. Good Luck! _______________________________________________________________________
Grading: Q.#
Score
(Max)
1.
__________ (72 pts)
2.
__________ (14 pts)
3.
__________ (11 pts)
4.
__________ (10 pts)
5.
__________ (12 pts)
6.
__________ (10 pts)
7.
__________ (14 pts)
8.
__________ (12 pts)
9.
__________ (15 pts)
10.
__________ (8 pts)
11.
__________ (6 pts)
12.
__________ (16 pts)
Total __________ (200)
Chem. 121
1.
Final Exam (5/7/07)
Name_____________________________________
(3 pts each) Please circle one answer for each question.
A. Which is the appropriate conversion from condensed formula to skeletal formula? (CH3)2ClCC(CH3)2COH(CH3)2 B.
A. Cl
OH
D. A and B
OH
C.
Cl
OH
Cl
E. All of the above
B. Indicate the hybridization of all of the second row elements in the following compound. A. B. C. D. E.
A-sp3; B-sp3; C-sp2; D-sp2; E-sp3 A-sp2; B-sp2; C-sp2; D-sp3; E-sp3 A-sp3; B-sp2; C-sp2; D-sp3; E-sp2 A-sp3; B-sp2; C-sp3; D-sp2; E-sp2 A-sp2; B-sp3; C-sp3; D-sp3; E-sp2
A
O
..
B
N
HN O
..
..
N H
D
..
N H
C
E
C.
Rank the following hydrogens (1, 2, and 3) in order of increasing acidity. 2 H A. 1, 2, 3 B. 2, 3, 1 C. 3, 2, 1 1 H D. 3, 1, 2 E. 2, 1, 3 3 H
D.
Which one of the following compounds has the highest boiling point? A. CH2 =CH(CH2 )4 CH3 B. CH3(CH2 )5 NH 2 C. CH3(CH2 )5 Cl D. (CH3 CH2 )3N E. CH3(CH2)5 Br
E.
Consider the molecule below, the nitrogen atom can best act as a A. electrophile .. B. nucleophile N C. base D. acid E. none of the above
Page 2
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Chem. 121
F.
Final Exam (5/7/07)
Name_____________________________________
Give the IUPAC name for the following compound. A. 1,1-diethyl-4-methyl-cyclohexane B. cis-1,1-diethyl-4-methyl-cyclohexane C. trans-1,1-diethyl-4-methyl-cyclohexane D. 3-(4-methyl-cyclohexyl)-pentane E. 3-ethyl-3,6,-ethyl-heptane
G.
Designate the following stereogenic centers as R or S (left side first). A. B. C. D. E.
S,R. S,S. R,S. R,R. None of the above. CH3 H HO CH2OH
A
Consider the following pairs of molecules: H.
Which pair of molecules represents a pair of enantiomers? B
I.
J.
Which pair of molecules does not represent isomers?
H CH2OH H
HOH2C
CH3 H HO CH2OH
OH H HOH2C CH3
C
CH2OH H HO CH2OH
HOH2C
D
CH3 H HO CH2OH
OH CH3 HOH2C H
H CH2OH H
An achiral compound that contains tetrahedral stereogenic centers is called: A. a diastereomeric molecule B. an orto C. a tetrameric molecule D. a stereogenic molecule E. a meso
K.
Which of the following is a meso compound?
A
B
C
D Page 3
E %
Chem. 121
L.
Exam II (3/21/07)
What is the correct stereochemical assignment for each of the following alkenes?
F
F
A A. B. C D. E. M.
C
D
A = E; B = Z; C = E; D = Z A = Z; B = E; C = E; D = E A = E; B = E; C = Z; D = Z A = E; B = E; C = Z; D = E A = E; B = E; C = E; D = E
R,R-4-chloro-2-hydroxyl-2,3,3,4-tetramethyl-pentane S,R-4-chloro-2-hydroxyl-2,3,3,4-tetramethyl-pentane R,S-2-chloro-2,3,3,4-tetramethyl-pentanol 4-chloro-2,3,3,4-tetramethyl-2-pentanol R,R-4-chloro-2,3,3,4-tetramethyl-2-pentanol
Cl OH
Predict the two most likely mechanisms for the reaction of 3-iodopentane with potassium tertbutoxide in DMSO (an aprotic solvent). A. B. C. D. E.
O.
B
What is the IUPAC name of the following molecule? A. B. C. D. E.
N.
Name_____________________________________
SN2 and SN1 E1 and E2 SN2 and E2 E1 and SN1 E2 and SN1
When S-2-bromobutane undergoes an SN1 reaction with methanethiol (CH3SH), what configuration(s) is/are present in the product? A. S only B. R only C. 50%:50% mixture of R and S D. Meso E. None of the above
Page 4
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Chem. 121
P.
OH
?
CH3
Br
H3C
NaH, CH3I PBr3, then CH3I CH3OH O3, CH3SCH3 A and C
The rate equation that describes the reaction shown below is: A. B. C. D. E.
T.
Br2, peroxides NaH, CH3CH2Br TsCl, then NaBr PBr3 C and D
A suitable method for converting 1-butanol to butyl methyl ether is: A. B. C. D E
S.
a C-H bond breaks a Br-H bond forms a C-Br bond forms a Br-Br breaks a C-C bond breaks
Which set of reaction conditions will provide the indicated product? A. B. C. D. E.
R.
Name_____________________________________
Which of the following does not occur in the propagation phase of free radical bromination of ethane to form bromoethane? A. B. C. D. E.
Q.
Exam II (3/21/07)
k[A] k[C][D] k[B] k[A][B] k([C][D]/[A][B])
Br +
A
NaOCH3
B
+
NaBr
C
D
The reaction between (CH3)3CI and CH3CH2OH to give (CH3)3COCH2CH3 is an example of: A. B. C. D. E.
S N2 S N1 Oxidation Addition E1 Page 5
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Chem. 121
U.
h!
Cl +
Cl2
2 3 4 5 6
How many propagation steps are required in the radical polymerization of venyl chloride to for the following PVC (poly-vinylchloride)? A. B. C. D. E.
X.
2 3 4 5 6
How many degrees of unsaturation are present in a compound with molecular formula C13H24? A. B. C. D. E.
W.
Name_____________________________________
How many products (including stereoisomers) would you expect to obtain upon mono-chlorination of the indicated substrate under the conditions shown? A. B. C. D. E.
V.
Exam II (3/21/07)
2 3 4 5 6
Cl RO
Cl
Cl
Cl OR
How many initiation steps are required in the radical polymerization of vinyl chloride to form the following PVC (poly-vinylchloride)? A. B. C. D. E.
2 3 4 5 6
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
2. A.
(8 pts) List the four main intermolecular forces between organic molecules from weak to strong.
1. __________________________________
2. __________________________________
3. __________________________________
4. __________________________________
B.
(6 pts) Ionophores selectively allow ions to cross biological membranes. List the three most important properties of the ionophore?
1. __________________________________
2. __________________________________
3. __________________________________
Page 7
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
3. A. (2 pts) Circle all the nucleophilic atoms in the following molecule. B. (5 pts) Draw all the possible resonance structures for this molecule.
O -O
NH2
C. (4 pts) The Ka of acetone (2-propanone: CH3 COCH3) is 10-20 and the pKa of propane is 50. Which one is more acidic?
Page 8
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
4. A. (6 pts) The following compound has another chair conformation. Which conformation is more stable? What is the distribution of these two conformers?
B. (4) Name this compound: __________________________________________________________ 5. A. B.
(2 pts) How many stereogenic centers does the following compound have? The specific rotation of the commercial drug l-Dopleron is [α] = -10˚*ml*g-1*dm-1. For a newly synthesized sample of Dopleron, the measured α was + 0.2˚ (1 dm cell), and the percentage of d- and of l-Dopleron was 55 % and 45%, respectively. 1. (4 pts) What is the ee in this sample?
2. (6 pts) What is the concentration of total Dopleron in this sample (show your calculations)?
Page 9
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
6. A. (6 pts) Which of the following molecules contain a poor leaving group (circle all that apply)? 1. CH3CH2CH2CH2Cl
2. CH3CH2CH2OH
3. CH3CH2CH2OHZnCl2
4. CH3CH2CH2OTs
5. CH3CH2CH2OCH3
B. (4 pts) Complete the sentence: In ________________________ reactions, the stability of the product has little effect on the energy of the transition state. However, in _______________________ reactions it has substential effect on the energy of the transition state.
7. (14 pts) Supply the missing products and reagents. A
E O3, then (CH3)2S
NBS, h!
B
D
HBr
C
C
G
H2SO4, HgSO4 H2O
Br2
C
NaH, then CH3Br
F
A
E
B
F
C
G
D
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
8. Use the reaction coordinate diagram below to answer the following questions.
2
3
4
1 5
a) (2 pts) How many intermediates are there in the reaction?
b) (2 pts) How many endothermic steps are there in the reaction?
c) (2 pts) Is the overall reaction exothermic or endothermic?
d) (2 pts) Does transition state structure 2 more closely resemble 1 or 3?
e) (2 pts) What effect will increasing the rate of reaction for 1 going to 3 have on the rate of the overall reaction?
f) (2 pts) What kind of reaction mechanism is illustrated in the energy diagram?
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Chem. 121
9.
Exam II (3/21/07)
Name_____________________________________
(15 pts) Draw only the main product of the following reactions: OTs
NaOC(CH3)3
1. CH3CH2ONa O
2. H2O
HBr
2 equiv HBr
KMnO4 H2 O
Page 12
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
10. (8 pts) Draw the mechanism for the following rearrangement:
H2SO4
11.
(6 pts) In which steps of the radical polymerization of vinyl chloride to form PVC (poly-vinylchloride) were bonds A and B formed? A
B
Cl
A. ____________________________________
RO
Cl
Cl
Cl OR
B. ____________________________________
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Chem. 121
Exam II (3/21/07)
Name_____________________________________
12. A. (10 pts) Synthesize 2-propene-1-ol from organic compounds with no more than two carbons (no limitations on other atoms, e.g., halides, oxygen, etc.). Draw all precursors (intermediates) and indicate the reagents used.
B. B. (6 pts) Use the 2-propene-1-ol (part A above) to synthesize S-3-methoxy-propane-1,2-diol in no more than three steps. Draw all precursors (intermediates) and indicate the reagents used. OH O
Page 14
OH
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