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Name: __________________________ Date: _____________
Cl NaOEt
CH3 ?
CH3
A)
OEt
CH3
CH3
B)
CH 3
CH 3
C)
CH3
CH3
D)
CH 3
OEt
CH 3
E)
CH2
CH3
Page 1
2. If the concentration of NaOH is doubled in the following reaction, what will happen to
the reaction rate?
H CH3
NaOH H
Br H
A) no change
B) double
C) quadruple
D) cut in half
E) None of the above.
3. The major product of the following reaction conditions will result from:
CH3CH2 CH3
NaN3
Br ?
A) SN2
B) SN1
C) E2
D) E1
E) there is no way to know
N
C)
N
D)
N
E)
Page 2
5. To which side, if any, would the following equilibrium lie? (Do not consider any further
reactions here.)
CH3 CH3
H3C C Br H3C C+ + Br
-
CH3 CH3
A) to the left
B) to the right
C) equally to the right and left
D) there is no way to tell
E) this reaction cannot occur at all
A) CH2OC(CH3)3
B) CH3
OC(CH 3)3
C) CH3
D) CH2
E) CH2OH
Page 3
7. Which would be true of the following reactions?
8. Which of the haloalkanes below would you expect to most rapidly undergo the reaction
shown?
H2O
RX ROH + HX
acetone
A) CH3CH2Br
B) CH3Br
C) (CH3)3CBr
D) CH3CHBrCH3
E) Br
9. Which of the bases below would be best to accomplish the following reaction?
?
CH2 CH2 CH2Br
CH2 CH CH2
A) CH3O– Na+
B) CH3CH2O– Na+
C) (CH3)2CHO– Na+
D) (CH3)3CO– Na+
E) Na+ –OH
Page 4
10. Which of the following molecules will readily undergo an elimination reaction when
treated with NaOCH3?
A)
Br
B)
Cl
C)
Br
D) H
Br
Page 5
12. Which of the cyclohexyl bromides would you expect to react the fastest in the following
reaction?
CH3O- Na+
alkyl bromide ?
CH3OH
A) H
Br
H
H
D
B) H
Br
D
H
H
C) Br
H
H
H
D
D) Br
H
D
H
H
E) All would react at the same rate.
Page 6
13. Predict the major product of the following SN1 reaction:
Br Ph EtOH
?
A) EtO Ph
B) Ph
C) Ph
D) Ph OEt
E)
14. Which one of the following would undergo E2 elimination most rapidly?
A)
Br
B)
Br
C)
Br
D) Br
Page 7
15. Which of the nucleophiles shown below would not cause an E2 elimination as the
predominant reaction?
Cl Nu
?
A) NaNH2
B) CH3CH2OH
C) -CN
D) -OH
E) CH3O-
16. How many alkene products are possible in the following reaction?
Page 8
18. Predict the major product of the following reaction:
CH3
Ethanol
H3C Br
heat
CH3
A) H CH 3
H CH 3 only
B) CH3
H3C OH
CH3
C) CH 3
H 3C OEt
CH 3
only
D) H3C CH CH CH3
E) CH 3
H CH 3
H 3C OEt
H CH 3 and CH 3
Page 9
19. (S)-1-bromo-1-fluoroethane reacts with NaOMe to give:
1 Eq. NaOMe
H 3C CHBrF
A) Br
CH2
H
B) F
CH2
H
C) CH3CHFOCH3
D) CH3CHBrOCH3
E) CH3CH(OCH3)2
Page 10
20. Predict the product of reaction of the following deuterated compound.
H
CH3 NaOCH3
Br
MeOH
H
D H
A) H
CH3
H
B) H
CH3
D
C) CH3
H
H D
D) H
CH3
OCH 3
H
D H
E) H
CH3
H
OCH 3
D H
Page 11
21. Rank the following carbocations according to their increasing stability.
A) A<B<C<D
B) A<C<B<D
C) C<A<B<D
D) A<C<D<B
E) None of the above.
22. Rank the following according to their increasing reactivity with water.
CH3 CH2Br CH3 Br (CH3)3 CBr (CH3)2 CHBr
A) CH3Br < CH3CH2Br < (CH3)3CBr < ( CH3)2CHBr
B) CH3Br < CH3CH2Br < ( CH3)2CHBr < (CH3)3CBr
C) (CH3)3CBr < ( CH3)2CHBr < CH3CH2Br < CH3Br
D) All of these will react with water at the same rate.
E) None of the above will react with water.
Page 12
23. For the transformation below, give the structure of the starting material.
LiN OLi
CH3
? 2
CH3
O
A) O
CH3
CH3
B) OH
C) OH
CH2
D) OH
CH3
CH3
E) OCH3
CH3
CH3
24. For the transformation below, give the structure of the starting material.
NaOCH3 H CH3
A) Br
B) Br
C)
Br
D) Br
Br
E) Both B and C will provide the product shown.
Page 13
25. For the transformation of norepinephrine to epinephrine (adrenaline), what is the likely
mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) both A and B are likely
Page 14
Answer Key
1. E
2. B
3. B
4. E
5. A
6. D
7. A
8. C
9. D
10. C
11. D
12. D
13. E
14. A
15. B
16. C
17. D
18. E
19. C
20. A
21. D
22. B
23. D
24. E
25. B
Page 15
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Compiler: R. H. Gretton
Language: English
COMPILED BY
R. H. GRETTON
FORMERLY DEMY OF MAGDALEN COLLEGE, OXFORD
AUTHOR OF "A MODERN HISTORY OF THE ENGLISH PEOPLE"
LONDON
G. BELL & SONS, LTD.
1913
INTRODUCTION
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History of England for Schools, Part I., by Keatinge and Frazer, pp.
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The order of the extracts is strictly chronological, each being
numbered, titled, and dated, and its authority given. The text is
modernized, where necessary, to the extent of leaving no difficulties
in reading.
We shall be most grateful to teachers and students who may send
us suggestions for improvement.
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