chem 3371 fall 2014 exam ii name:faculty.smu.edu/alippert/examii-fall2014.pdf · chem 3371 fall...
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Chem 3371 Fall 2014 Exam II Name: _________________________
Page (1 of 14)
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (2 of 14)
Grade Sheet: Page 3: ____________ (6 pts) Page 4: ____________ (8 pts) Page 5: ____________ (6 pts) Page 6: ____________ (6 pts) Page 7: ____________ (4 pts) Page 8: ____________ (18 pts) Page 9: ____________ (18 pts) Page 10: ____________ (10 pts) Page 11: ____________ (14 pts) Page 12: ____________ (10 pts) Page 13: ____________ (10 pts) Total: ____________ (110 pts)
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (3 of 14)
1. (2 pts) Classify the reaction below. (circle the best answer)
A. Substitution B. Elimination C. Addition D. none of the above 2. (2 pts) Classify the reaction below. (circle the best answer)
A. Substitution B. Elimination C. Addition D. none of the above 3. (2 pts) Classify the reaction below. (circle the best answer)
A. Substitution B. Elimination C. Addition D. none of the above 4.–6. Use the chart of equilibrium constants below to answer quetsions 4.–6.
+ N3
NN
N
OH
OTs
O
OH
OH O
R
H
H
R
(axial) (equatorial)
R
CH3
CH2CH3
CH(CH3)2
C(CH3)3
18
23
38
4000
Keq
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (4 of 14)
4. (2 pts) Which R group shows the highest percentage of equatorial conformation at equilibrium? (circle the best answer):
5. (2 pts) Which R group shows the highest percentage of axial conformation at equilibrium? (circle the best answer):
6. (2 pts) Which R group has the most negative ΔGº? (circle the best answer):
7. (2 pts) For which of the following reactions will ΔSº have a significantly positive value (circle ALL that apply, there could be more than one answer):
CH3
CH2CH3
CH(CH3)2
C(CH3)3
A.
B.
C.
D.
E. none of the above
CH3
CH2CH3
CH(CH3)2
C(CH3)3
A.
B.
C.
D.
E. none of the above
CH3
CH2CH3
CH(CH3)2
C(CH3)3
A.
B.
C.
D.
E. none of the above
A.
B.
C.
D.
E. none of the above
+
CH3• + CH3• CH3CH3
CH3COOCH3 + H2O CH3COOH + CH3OH
OHOO OH
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (5 of 14)
8. (2pts) Name the structure below (circle the best answer):
A. (7R)-7-iodo-4-isobutyl -2,3-dimethyloctane B. (7R)-4-sec-butyl-7-iodo-2,3-dimethyloctane C. (7S)-7-iodo-4-isobutyl -2,3-dimethyloctane D. (7S)-4-sec-butyl-7-iodo-2,3-dimethyloctane E. none of the above 9. (2 pts) Name the structure below (circle the best answer):
A. (2S,5R)-3-ethyl-2-methylheptan-6-ol B. (2S,5R)-5-ethyl-6-methylheptan-2-ol C. (2R,5S)-3-ethyl-2-methylheptan-6-ol D. (2R,5S)-5-ethyl-6-methylheptan-2-ol E. none of the above 10. (2 pts) Which alkyl halide will undergo the fastest SN2 reaction (circle the best answer)?
I
OH
I
Br
Cl
Br
A.
B.
C.
D.
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (6 of 14)
11. (2 pts) Which alkyl halide will undergo the fastest SN1 reaction (circle the best answer)?
12. (2 pts) What is/are the major product(s) of the SN2 reaction below (circle ALL that apply, there could be more than one answer)?
13. (2 pts) What is/are the major product(s) of the SN1 reaction below (circle ALL that apply, there could be more than one answer)?
I
Br
Cl
Br
A.
B.
C.
D.
I+ NH2
A. B. C. D. E. none of the above
NHNH NHNH
IOH
OCH3
A. B. C. D.
E. none of the above
O
OCH3
O
OCH3
O
OCH3
O
OCH3
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (7 of 14)
14. (2 pts) For the E2 reaction below, identify the MAJOR product (circle the best answer).
15. (2 pts) For the E2 reaction below, identify the MAJOR product (circle the best answer).
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (8 of 14)
16. (4 pts) Which mechanisms would you predict for the following reaction (circle ALL that apply, there could be more then one answer):
A. SN1 B. SN2 C. E1 D. E2 E. none of the above 17. (4 pts) Which mechanisms would you predict for the following reaction (circle ALL that apply, there could be more then one answer):
A. SN1 B. SN2 C. E1 D. E2 E. none of the above 18. (4 pts) Which mechanisms would you predict for the following reaction (circle ALL that apply, there could be more then one answer):
A. SN1 B. SN2 C. E1 D. E2 E. none of the above 19. (3 pts) Which mechanisms would you predict for forming the indicated product in the following reaction (circle ALL that apply, there could be more then one answer):
A. SN1 B. SN2 C. E1 D. E2 E. none of the above 20. (3 pts) Which mechanisms would you predict for forming the indicated products in the following reaction (circle ALL that apply, there could be more then one answer):
A. SN1 B. SN2 C. E1 D. E2 E. none of the above
Br + KCN
I + KOC(CH3)3
Br CH3CH2OH
HO
pTSA:S
O
O
OH
H3C
OHH2SO4
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (9 of 14)
Section 2: Drawing Structures 21. (4 pts) Draw two unique resonance structures for the molecule drawn below.
22. (4 pts) Draw two unique resonance structures for the molecule drawn below.
23. (5 pts) Assume the reaction below goes by an SN2 mechanism. Draw the mechanism and products. Be sure to indicate the stereochemistry.
24. (5 pts) Assume the reaction below goes by an E2 mechanism. Draw the mechanism and products. Be sure to indicate the stereochemistry.
NO
O
O
Cl + KCNDMSO
Cl + KOC(CH3)3DMSO
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (10 of 14)
25. (5 pts) Draw the two major products from an SN1 reaction below in box A and B. Then draw a stepwise mechanism to form product A.
26. (5 pts) Draw the four major products formed from an E1 reaction below in boxes A B, C, and D. Then draw a stepwise mechanism to form product A.
Br HOCH2CH3
A B
Br HOCH2CH3
A B
C D
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (11 of 14)
27. (5 pts) Draw a stepwise mechanism for the reaction below.
28. (3 pts) Draw the two major elimination products from the following reaction. Be sure to indicate stereochemistry.
29. (3 pts) Draw the major product(s) from the following reactions.
30. (3 pts) Draw the major products from the following reactions nucleophilic substitution reactions. Be sure to indicate stereochemistry.
H2SO4
OH
OH POCl3
pyrdine:N
Major Minor
OH SOCl2PBr3
O1. NaOCH3CH32. H2O
HOCH2CH3H2SO4
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (12 of 14)
31. (10 pts) Your laboratory is stocked with the chemicals below. Using only these reagents and any solvents you need, show a stepwise synthesis of the alkyne below:
OHH H OH HBr NaH
SOCl2 PBr3
N SO
O
Cl
H3C
Your reagents and starting materials:
Your synthetic target:
H H +
OH+
Intermediate A
Intermediate A
+
OH +
+
+
Chem 3371 Fall 2014 Exam II Name: _________________________
Page (13 of 14)
32. (10 pts) Synthesize the compound below from 2-bromocyclohexanol. You may use any necessary reagents and any organic compounds with 2 carbons or less.
N3
HO
Br
HO+ any reagent and organic compoundswith 2 carbons or less
Chem 3371 Fall 2014 Exam II Name: _________________________
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