Download SCI2199 - Introduction to Organic Chemistry II

SCI2199 - Introduction to Organic Chemistry II - Fall 2016
Homework 2
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1. Which of the following could not be used to synthesize 2-bromopentane efficiently?
A) 1-Pentene + HBr →
B) 2-Pentene + HBr →
C) 2-Pentanol + HBr →
D) 2-Pentanol + PBr3 →
E) All of these choices would afford good yields of 2-bromopentane.
2. trans-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of base. The
product of this reaction is then heated with KI in methanol. What is the final
product?
A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene
3. What would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
I
II
III
IV
An equimolar mixture of I and II.
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4. What would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
I
II
III
IV
An equimolar mixture of I and II.
5. Which of the following could be used to synthesize 1-bromopentane?
A) CH3CH2CH2CH=CH2 + HBr →
B) CH3CH2CH2CH2CH2OH + PBr3 →
C) CH3CH2CH2CH2CH2OH + NaBr →
D) CH3CH2CH2CH2CH2OH + Br2 →
E) CH3CH2CH2CH=CH2 + Br2 →
6. What would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
I
II
III
IV
An equimolar mixture of I and II.
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7. Which of the following could be used to synthesize 2-bromobutane?
A) CH3CH2CH=CH2 + Br2(aq) →
B) CH3CH2CHOHCH3 + HBr →
C) CH3CH2C≡CH + HBr →
D) CH3CH2C≡CH + Br2 →
E) More than one of these choices.
8. Which of the alcohols listed below would you expect to react most rapidly with
PBr3?
A) CH3CH2CH2CH2CH2CH2OH
B) (CH3CH2)2CH(OH)CH2CH3
C) (CH3CH2)2CHOHCH3
D) (CH3CH2)3COH
E) (CH3CH2)2C(CH3)OH
9. cis-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of a base. The
product of the reaction then is allowed to react with KI in methanol. What is the final
product?
A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene
10. The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4methylpentane is probably:
A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the
alcohol as the substrate.
B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the
alcohol as the substrate.
C) an E1-type reaction involving the protonated alkyl dibomophosphite of the
alcohol as the substrate.
D) an E2-type reaction involving the protonated alkyl dibomophosphite of the
alcohol as the substrate.
E) an epoxidation reaction.
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11. Which compound is a mesylate?
A)
B)
C)
D)
E)
I
II
III
IV
V
12. The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2methylpentane is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
13. Which alcohol would undergo acid-catalyzed dehydration most rapidly?
A) 3,3-dimethyl-1-butanol
B) 2,2-dimethyl-1-butanol
C) 3,3-dimethyl-2-butanol
D) 2-methyl-2-butanol
E) All would undergo dehydration equally rapidly.
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14. What would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
I
II
III
IV
An equimolar mixture of I and II.
15. Which reagent(s) would transform propyl alcohol into propyl bromide?
A) Concd. HBr and heat
B) PBr3
C) NaBr/H2O and heat
D) More than one of these choices.
E) All of these choices.
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16. What would be the major product of the following reaction sequence?
A)
B)
C)
D)
E)
I
II
III
IV
An equimolar mixture of II and III.
17. Which of the following could be used to synthesize 2-bromobutane?
A)
B)
C)
D)
E)
More than one of these choices.
18. The reaction between 1-pentanol and HBr to yield 1-bromopentanol is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
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19. Which of the alcohols listed below would you expect to react most rapidly with HBr,
assuming the reaction pathway is predominantly SN1?
A) CH3CH2CH2CH2CH2CH2OH
B) (CH3CH2)2CH2CH2OH
C) (CH3)2CHCH2CHOHCH3
D) CH3CH2CH2CH2CH2OH
E) (CH3CH2)2C(CH3)OH
20. Which of the following could be used to synthesize 2-chlorobutane?
A)
B)
C)
D)
E)
None of these choices.
21. The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene is
probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
22. Which of the following could be used to synthesize 2-chlorobutane?
A) CH3CH2CH=CH2 + Cl2(aq) →
B) CH3CH2CHOHCH3 + HCl →
C) CH3CH2C≡CH + HCl →
D) CH3CH2C≡CH + Cl2 →
E) None of these choices.
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23. The conversion of
is best
achieved through use of which of these reagents in a low temperature reaction?
A) Concd. HBr
B) Br2
C) NaBr, H2SO4
D) PBr3
E) HBr, peroxide
24. Assuming the mechanistic pathway for each of the following reactions is
predominately SN1, which of these alkyl halide syntheses is predicted to occur at the
greatest rate?
A) CH3CH2CH2CH2OH + HI →
B) (CH3)2CHCH2OH + HBr →
C) CH3CHOHCH2CH3 + HCl →
D) CH3CHOHCH2CH3 + HBr →
E) (CH3)3COH + HI →
25. Which of the following reactions would serve as a synthesis of butyl bromide?
A)
B) CH3CH2CH2CH2OH + PBr3 →
C)
D) CH3CH2CH2CH2OH + Br2 →
E) Two of these choices.
26. The reaction between 4-methyl-1-pentanol and HBr to yield 4-methyl-1-pentene is
probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
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27. Which compound is a tosylate?
A)
B)
C)
D)
E)
I
II
III
IV
V
28. The conversion of 3-methyl-1-octanol to 1-chloro-3-methyloctane is best achieved
through use of which of these reagents?
A) Concd. HCl
B) SO2Cl2
C) NaCl, H2SO4
D) PCl3
E) POCl3
29. Which of the following could be used to synthesize 2-iodobutane?
A) CH3CH2CH=CH2 + I2(aq) →
B) CH3CH2CHOHCH3 + HI →
C) CH3CH2C≡CH + HI →
D) CH3CH2C≡CH + I2 →
E) None of these choices.
30. Which of the following could be used to synthesize 1-bromobutane efficiently?
A) CH3CH2CH=CH2 + HBr →
B) CH3CH2CH2CH2OH + PBr3 →
C) CH3CH2CH2(OH)CH3 + HBr →
D) CH3CH2CH2CH2OH + Br2 →
E) None of these choices.
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31. The following reaction,
is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
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