SCI2199 - Introduction to Organic Chemistry II - Fall 2016
Homework 3
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1. Which method would provide the best synthesis of ethyl isopropyl ether?
A) (CH3)2CHONa + CH3CH2Br →
B) CH3CH2ONa + (CH3)2CHBr →
C)
D)
E)
CH3CH2ONa + (CH3)2CHOH →
2. Propose a mechanism for the following transformation:
3. What would be the major product(s) of the following reaction
A)
B)
C)
D)
E)
C6H5Br + CH3OH
C6H5CH2Br + CH3Br
C6H5CH2OH + CH3Br
C6H5CH2Br + CH3OH
C6H5CH2CH2Br
4. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THFethanol mixture and the resulting product reacted with NaBH4 in basic solution, the
principal product formed is which of these?
A) 3-methyl-3-pentanol
B) 3-ethoxy-3-methylpentane
C) 3-methyl-2-pentanol
D) 2-ethoxy-3-methylpentane
E) 1-ethoxy-3-methylpentane
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5. Which is the best method for the synthesis of tert-butyl methyl ether?
A) CH3ONa + (CH3)3CBr →
B) (CH3)3CONa + CH3I →
C)
D) (CH3)3CONa + CH3OCH3 →
E) CH3ONa + (CH3)3COH →
6. Propose a mechanism for the following transformation:
7. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
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8. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
9. Which is the best way to prepare 3-methoxypentane via the Williamson method?
A) CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140 °C
B) CH3OH + (CH3)2CHCH2CH2OH + H2SO4, 140 °C
C) CH3ONa + (CH3CH2)2CHBr
D) CH3I + (CH3CH2)2CHONa
E) CH3I + (CH3)2CHCH2CH2ONa
10. Which of these ethers is least likely to undergo significant cleavage by hot aqueous
H2SO4?
A)
B)
C)
D)
E)
I
II
III
IV
V
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11. Heating 2-ethoxyhexane with excess concentrated HBr would produce:
A) CH3CH2OCH2CH2CH2CH2CH2CH2Br
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2Br and CH3CH2CH2CH2CHBrCH3
12. Heating 2-ethoxyhexane with one equivalent of concentrated HI would produce:
A) CH3CH2OCH2CH2CH2CH2CH2CH2I
B) ICH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHICH3
D) CH3CH2I and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2I and CH3CH2CH2CH2CH(OH)CH3
13. Propose a mechanism for the following transformation:
14. Heating 2-ethoxyhexane with one equivalent of concentrated HBr would produce:
A) CH3CH2OCH2CH2CH2CH2CH2CH2Br
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2Br and CH3CH2CH2CH2CH(OH)CH3
15. Propose a mechanism for the following transformation:
16. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THFt-butyl alcohol mixture and the resulting product reacted with NaBH4 in basic
solution, the principal product formed is which of these?
A) 3-methyl-3-pentanol
B) 3-t-butoxy-3-methylpentane
C) 3-methyl-2-pentanol
D) 2-t-butoxy-3-methylpentane
E) 1-t-butoxy-3-methylpentane
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17. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
18. Which is the most efficient way to prepare isopropyl methyl ether via the Williamson
method?
19. Which is the best method to prepare ethoxycyclopentane via the Williamson
method?
20. Propose a mechanism for the following transformation:
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21. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
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22. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
23. What would be the major product(s) of the following reaction
A)
B)
C)
D)
E)
C6H5Br + CH3OH
C6H5CH2Br + CH3Br
C6H5CH2OH + CH3Br
C6H5CH2Br + CH3OH
C6H5CH2CH2Br
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24. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
25. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
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26. Propose a mechanism for the following transformation:
27. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
28. Which is the best method to prepare 2-ethoxy-5-methylhexane?
A) C2H5ONa + (CH3)2CHCH2CH2Br
B) C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br
C) C2H5ONa + (CH3)2CHCH2CH2CHBrCH3
D) C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa
E)
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29. The product(s) of the following reaction
A)
B)
C)
D)
E)
I
II
III
IV
None of these choices.
30. Predict the product of the following reaction:
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