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1. What is the major product of the reaction, (CH3)3COK ? (CH3)3COH heat Br A) (CH3)2C=C(CH3)2 B) (CH3)3CCH=CH2 C) (CH3)2C=CHCH3
2. By analyzing the starting material and the product(s), the following reaction is possibly an example of what type of mechanism?
+
Br N3 N3
A) SN1
B) SN2
C) E1
D) E2
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3. I and II are:
H H3CH2C Br OH Cl CH2CH2CH3 Cl HO CH2CH2CH3 Br H CH2CH3
A)
OH
D)
+ enantiomer
O
+ HCHO
E)
OH
B)
C)
OH
5. Which of the following carbocations would NOT be likely to undergo rearrangement? CH3 D) A) CH3CHCHCH3
B)
CH3 CH3
E)
CH3CHCH2 CH3
CH3CHCCH3 CH3
C)
CH3CCHCH2CH3 CH3
CH3 CH3CCH2CH3
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H3C H
CH3 Br
H3C H
CH3 OCH3
H3C H
OCH3 CH3
II
H3C
CH3
H3C
A) I
III B) II
C) III and IV
IV D) I and II
A)
+ enantiomer
O
D)
B)
+ enantiomer
O OH
E)
C)
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A) the same melting point. B) different melting points. C) equal but opposite optical rotations.
(1 mol) NaNH2
(1 mol)
Br
CH3OH
Br
D)
OH
HA heat
Br
E)
NaOC2H5 C2H5OH
10. What is the major product for the following reaction sequence? 1a. NaNH2, NH3 (liq.) 1b. CH3CH2CH2Br
D)
B) C)
E)
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11. What will be the major product of the following reaction? 85% H3PO4 ? heat
OH
A)
D)
B)
E)
C)
Cl
NaCN
CN
NaCl
Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5-methylhexane and CN ion? A) No effect. D) It would increase the rate four times. B) It would double the rate. E) It would increase the rate six times. C) It would triple the rate.
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A)
+ enantiomer
OH
D)
OH
B)
H
OH O
E)
+ enantiomer
O
OH
C)
+ enantiomer
OH
OH SN2
C H 2O H H 3C O CH3 H H
C H 2O H OCH3 CH3
I
C H 2C l HO CH3 H H
II
C H 2C l OH CH3
III
IV
A) I
B) II
C) III
D) IV
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HBr
A)
+ enantiomer
Br
B)
+ enantiomer
Br Br
C) D)
+ enantiomer
+ enantiomer
Br
E)
A)
D)
B) C)
E)
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18. Predict the product(s) for the following reaction sequence. 1. NaI, acetone
Cl
A)
2. CH3CO2Na, CH3CO2H D)
B)
O O
E)
A mixture of A) and D)
C)
O O
19. Which statement is not true for a meso compound? A) The specific rotation is 0. B) There are one or more planes of symmetry. C) A single molecule is identical to its mirror image. D) More than one stereogenic center must be present. E) The stereochemical labels, (R) and (S), must be identical for each stereogenic center.
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21. The correct IUPAC name for the following compound is:
Cl
Br
A) B) C) D) E)
22. What can be said with certainty if a compound has [] 25 = -9.25 ? D A) The compound has the (S) configuration. B) The compound has the (R) configuration. C) The compound is not a meso form. D) The compound possesses only one stereogenic center. E) The compound has an optical purity of less than 100%.
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Answer Key
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22.
B A D E C C D B B C A D E B C B B C E D A C
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