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CEM252, Fall 2009 Midterm #1
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CEM 252, Fall 2009 Tue, Thurs 8:00–9:20 am
Midterm #1 October 1, 2009
Name:______________________________ PID: _______________________________
Section:____________ TA: _______________
This is a closed book and note examination. If boxes are provided for your answers, only what is written in the boxes will be graded. You have 80 minutes to complete the test.
Question Points Score 1 8 2 10 3 6 4 4 5 6 6 4 7 6 8 6 9a 16 9b 16 10a 6 10b 6 10c 6
Total 100
Section 1 M 8:00 – 8:50 AM Roozbeh Section 2 W 8:00 – 8:50 AM Aman Section 3 W 1:50 – 2:40 PM Aman Section 4 M 11:30 – 12:20 PM Roozbeh Section 5 F 9:10 – 10:00 AM Wenjing Section 6 M 11:30 – 12:20 AM Atefeh Section 7 F 3:00 – 3:50 PM Wenjjing Section 8 M 9:10 – 10:00 AM Roozbeh Section 9 Th 4:10 – 5:00 PM Atefeh Section 10 F 8:00 – 8:50 AM Wenjing Section 11 W 9:10 – 10:00 AM Aman Section 12 Th 1:50 – 2:40 PM Atefeh
CEM252, Fall 2009 Midterm #1
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1. Provide a name or a structure for the following compounds (2 pts each, 8 pts) a. 2,3-epoxy-4-nitro-1-phenyl pentane b. m-nitro benzoic acid c. d. 2. Match the following names with their appropriate structures (write the letter corresponding to the structure beside the given name) (NOTICE there are more structures than names and ONLY 1 correct answer) (2 pts each, 10 pts)
A B
NH
N
OHNH2
C
E F G
H I J
O OH
D
NHO
OH
OH
OH
OHHN
K
O O
L M N O
OO
1,4 cyclohexane diol
Benzyl isopropyl ether
Name Letter Naphthalene G Glycerol K Pyrrole I Indole E Toluene C
O
HO
OH
ONO2
NO2
OH
O
CEM252, Fall 2009 Midterm #1
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3. Determine where the chlorine would add to the following substituted benzenes (there could be more than one compound). (6 pts, 2 pts each box) 4. Write all the resonance structures of the following aromatic compound (4 pts).
(Bonus 2 pts, Circle the correct answer): Is the compound a o/p or m director?
O
SO3H
Cl2FeCl3
Cl2
FeCl3
Cl2
FeCl3
OH
SH
O
OH
Cl
OH
Cl
SO3HSO3HCl
Cl
SH
O
Cl
SH
O
SH
OCl
Cl
O O O O
CEM252, Fall 2009 Midterm #1
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5. Circle the correct answer. (2 pts each, 6 pts) a. Which of the following compounds is aromatic? b. Which of the following has the most acidic (lowest pKa) phenolic H (-OH)? c. Which of the following compounds is anti-aromatic? 6. As written the following syntheses have flaws. What is wrong with each of them? (4 pts, 2 pts each) a. b.
OH OH OH OHOH
O2N NO2
NO2
O2N NO2
NO2NH2
OH
O
1. CH3CH2MgBr
2. H3O+
OH
OH
Acidic proton, reacts with Grignard
CH3CH2
1. CH3OH, H+
2. NaH
3.
OO
O
Cl
Acidic opening
CH3OH, H+
O
OH
1. NaH
2.Cl
O
O
CEM252, Fall 2009 Midterm #1
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7. Show a detailed mechanism of the following transformation. (6 pts)
OH
H Cl
Cl
OH2
Cl
CEM252, Fall 2009 Midterm #1
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8. Determine the structure of the following compound based on the 1H-NMR spectrum and IR data given. Put your final structure in the box. (show work for partial credit). (6 pts) C12H19ON
1H-NMR: 1.25 ppm (t, 3H); 1.49 ppm (d, 3H); 2.60 ppm (q, 2H); 3.17 ppm (s, 3H); 4.30 ppm (q, 1H); 4.36 ppm (s, 2H); 7.10 ppm (3H); 8.68 ppm (broad singlet, 2H).
02468
PPM
3
12
2
3
3
23
O
NH2
CEM252, Fall 2009 Midterm #1
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9. Provide the major product or the reaction conditions for the following reactions. (32 pts, 2 pts each box)
a.
b.
c.
d.
e.
OH1. H2SO4, heat2. Hg(OAc)2, CH3OH3. NaBH4
NO2
SnHCl
O
Name the reaction for 2 bonus points
NBSH2O
O
Cl
O
AlCl3
Friedel Crafts Acylation
H2 / Pd
Br
NH2
1. OsO4, pyridine
2. NaHSO3
Show stereochemistry
OH
OH
OH
Cl
AlCl3
KMnO4 H2O
OH OH
OHO
CEM252, Fall 2009 Midterm #1
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g.
h.
i.
j.
f.
OH1. SOCl22. Mg, ether O
1.
2. H3O+
Name the reaction for 2 bonus points
OHCrO3
H2SO4, heatO
1. BH3, THF2. H2O2, NaOH
OH
Jones Ox.
OH
O
O
MgCl
OH
O
250 C
OH
mCPBA
O
H 1. NaBH4
2. H3O+
Draw the structure of mCPBA for 2 bonus pts
OH POCl3pyr
or H2SO4, heat
O
Cl
O
O
OH
CEM252, Fall 2009 Midterm #1
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10. Provide a reasonable synthesis for the following molecules using the given starting material and anything else you need. Several steps are required. (Show work for partial credit) (18 pts, 6 pts each) a.
OH
O
O2N
OH
O
O2N
KMnO4
H2OO2N
CH3Cl , AlCl3
H2SO4
HNO3
CEM252, Fall 2009 Midterm #1
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b.
OHO
O
1. NaBH4 (or LAH)
2. H3O+
OH
POCl3, pyror H2SO4, heat
mCPBAO
1. CH3CH2O Na
2. H3O+
CEM252, Fall 2009 Midterm #1
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c.
HOH
O
HO
O
O
TMSClpyr
TMSOH
O
1. CH3CH2MgBr
2. H3O+
HO
OH
Jones Oxidation
(CrO3, H2SO4, H2O)
CEM252, Fall 2009 Midterm #1
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Scratch Sheet: Needs to be turned in with the test (if missing, the test will not be graded)
