Organic Chemistry, 6e (Smith)

Chapter 9 Alcohols, Ethers, and Related Compounds

1) Which of the following compounds is (are) primary alcohols?

A) Only I
B) Only II
C) Only I and II
D) Only II and III

2) Which of the following compounds is (are) secondary alcohols?

A) Only I
B) Only II
C) Only II and III
D) Only III and IV

3) Which of the following compounds are ethers?

A) Only I and II
B) Only III and IV
C) Only I, II, and III
D) I, II, III, and IV

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4) Which of the following compounds are epoxides?

A) Only I and III

B) Only III and IV
C) Only I, III, and IV
D) I, II, III, and IV

5) Which of the following compounds is (are) symmetrical ethers?

A) Only I
B) Only IV
C) Only III and IV
D) Only I, III, and IV

6) Which of the following explains why epoxides are much more reactive than ethers?
A) The C-O-C bond angle of an epoxide is 109°, making epoxides to have angle strain.
B) The oxygen atom of an epoxide is sp2 hybridized.
C) The C-O-C bond angle of an epoxide is 120°, making epoxides to have angle strain.
D) The C-O-C bond angle of an epoxide is 60°, making epoxides to have angle strain.

7) What is the IUPAC of the following compound?

(CH3CH2)3COH
A) 2-Ethyl-2-pentanol
B) 2-Ethyl-3-pentanol
C) 3-Ethyl-3-pentanol
D) 2,2-Diethyl-1-butanol

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8) What is the IUPAC of the following compound?

A) 3,3,6-Trimethylcyclohexanol
B) 2,5,5-Trimethylcyclohexanol
C) 1,4,4-Trimethyl-2-cyclohexanol
D) 1,1,4-Trimethyl-2-cyclohexanol

9) What is the IUPAC of the following compound?

A) 5-Hydroxy-3-methyl-1-pentene
B) 3-Methyl-5-penten-1-ol
C) 3-Methyl-1-penten-5-ol
D) 3-Methyl-4-penten-1-ol

10) What is the IUPAC of the following compound?

A) (S)-2,2-Dimethyl-3-pentanol
B) (R)-2,2-Dimethyl-3-pentanol
C) (R)-4,4-Dimethyl-3-pentanol
D) (S)-1-tert-Butyl-1-propanol

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11) What is the IUPAC of the following compound?

A) Ethoxyoctane
B) 5-Ethoxyoctane
C) 4-Ethoxyoctane
D) Ethyl octyl ether

12) What is the common name of the following compound?

A) Isobutyl isopropyl ether

B) Diisobutyl ether
C) Di-sec-butyl ether
D) Diisopropyl ether

13) What is the common name of the following compound?

A) Methyl sec-butyl ether

B) Isobutyl methyl ether
C) sec-Butyl methyl ether
D) Butyl methyl ether

14) What is the common name of the following compound?

A) Methyl vinyl ether

B) Allyl methyl ether
C) Propenyl methyl ether
D) Methylene propylene ether

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15) What is the IUPAC of the following compound?

A) 1,2-Epoxy-4-methylcyclohexane
B) 3,4-Epoxy-1-methylcyclohexane
C) 1,2-Epoxy-3-methylcyclohexane
D) 1,2-Epoxy-5-methylcyclohexane

16) What is the IUPAC of the following compound?

A) 1,2-Epoxy-2-methylcyclopentane
B) 1,2-Epoxy-1-methylcyclopentane
C) 1,2-Epoxy-1-methylpentane
D) 1,2-Epoxy-2-methylpentane

17) What is the IUPAC of the following compound?

A) 1,1-Dimethyloxirane
B) 2-Methylpropylane
C) 2-Methylpropylene oxide
D) 2,2-Dimethyloxirane

18) Which of the following compounds has the highest boiling point?

A) I
B) II
C) III
D) IV
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19) Which of the following compounds has the highest boiling point?

A) I
B) II
C) III
D) IV

20) Rank the following compounds in order of increasing boiling point, putting the compound
with the lowest boiling point first.

A) III < II < I < IV

B) II < III < I < IV
C) IV < I < II < III
D) I < II < III < IV

21) Which of the following statements about a crown ether-cation complex is not true?
A) It is a host-guest complex.
B) The crown ether is the guest and the cation is the host.
C) The crown ether is the host and the cation is the guest.
D) The host-guest complex is soluble in nonpolar solvents.

22) Which of the following reactions will provide the best yield of ether by the Williamson
ether synthesis?
A) Sodium methoxide and tert-butyl bromide.
B) Sodium tert-butoxide and iodomethane.
C) Methanol and tert-butyl alcohol in the presence of KOH.
D) Iodomethane and tert-butyl bromide in the presence of KOH.

23) Which of the following reactions will provide the best yield of ether by the Williamson
ether synthesis?
A) Bromobenzene and sodium methoxide
B) Phenol and sodium methoxide
C) Bromobenzene and bromomethane
D) Sodium phenoxide and bromomethane

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24) Which of the following ethers cannot be prepared by the Williamson ether synthesis?
A) Isopropyl methyl ether
B) tert-Butyl methyl ether
C) tert-Butyl phenyl ether
D) Methyl phenyl ether

25) Which of the following would be a reasonable synthesis of 1-butanol?

A) I
B) II
C) III
D) IV

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26) Which of the following would be a reasonable synthesis of 2-butanol?

A) I
B) II
C) III
D) IV

27) What is the best choice of reagent to accomplish the following transformation?

A) HCl
B) SOCl2, pyridine
C) Cl2
D) H3O+, H2O

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28) What is the product of the following reaction?

A) I
B) II
C) III
D) IV

29) What is the major organic product(s) obtained in the following reaction?

A) I
B) II
C) III
D) I and II

30) What is the best choice of reagent to accomplish the following transformation?

A) HCl
B) H2SO4
C) NaOH
D) TsCl, pyridine

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31) Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl
halide?

A) I
B) II
C) III
D) IV

32) What is the major organic product obtained from the following sequence of reactions?

A) 2-Methyl-1-butene
B) 3-Methyl-3-butene
C) 1-Chloro-2-methylbutane
D) 1-Bromo-2-methylbutane

33) Determine the product(s) of the following reaction.

A) Only I
B) Only II
C) Only III
D) Only II and III

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34) Determine the product(s) of the following reaction.

A) Only I
B) Only II
C) Only III
D) Only I and II

35) Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the
least reactive first.

A) I < III < II

B) I < II < III
C) II < III < I
D) III < II < I

36) Which of the following statements about carbocation rearrangement is not true?
A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen
atom.
B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl
group.
C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation.
D) The migrating group in a 1,2-shift moves with one bonding electron.

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37) Which of the following alcohols is most likely to yield a carbocation that is susceptible to
rearrangements?

A) I
B) II
C) III
D) IV

38) What is the best choice of reagent to accomplish the following transformation?

A) TsCl, pyridine
B) POCl3, pyridine
C) HCl, ZnCl2
D) NaOH

39) What is the major organic product obtained from the following reaction?

A) I
B) II
C) III
D) IV

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40) What is the major organic product obtained from the following reaction?

A) (±)-2-Chlorobutane
B) (R)-2-Chlorobutane
C) (S)-2-Chlorobutane
D) trans-2-Butene

41) What is the major organic product obtained from the following sequence of reactions?

A) (R)-2-Methylpentanenitrile
B) (S)-2-Methylpentanenitrile
C) (±)-2-Methylpentanenitrile
D) trans-2-Butene

42) What is the major organic product obtained from the following sequence of reactions?

A) (S)-2-Methoxypentane
B) (R)-2-Methoxypentane
C) (±)-2-Methoxypentane
D) trans-2-Butene

43) What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?
A) Bromomethane and ethanol
B) Bromoethane and methanol
C) Bromoethane and bromomethane
D) Ethanol and methanol

44) What are the major products obtained upon treatment of tert-butyl methyl ether with excess
HI?
A) tert-Butyl alcohol and iodomethane
B) tert-Butyl iodide and iodomethane
C) tert-Butyl alcohol and methanol
D) tert-Butyl iodide and methanol

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45) Which of the following statements about the reaction of ethers with strong acids is true?
A) HCl, HBr, and HI can all be used.
B) The mechanism of ether cleavage is SN1 only.
C) The mechanism of ether cleavage is SN2 only.
D) The mechanism of ether cleavage is SN1 and SN2.

46) What are the major products obtained upon treatment of methyl phenyl ether with excess
HBr?
A) Phenol and bromomethane
B) Phenol and methanol
C) Bromobenzene and bromomethane
D) Bromobenzene and methanol

47) Determine the product in the following reaction (ignoring possible stereoisomers).

A) I
B) II
C) III
D) IV

48) Determine the product in the following reaction (ignoring possible stereoisomers).

A) I
B) II
C) III
D) IV

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49) What is the product of the following reaction?

A) I
B) II
C) III
D) IV

50) What is the major alkene formed when compound A is dehydrated with H2SO4?

A) I
B) II
C) III
D) IV

51) What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?

A) I
B) II
C) III
D) IV

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52) What is the major organic product of the following reaction?

A) I
B) II
C) III
D) IV

53) What is the major organic product of the following reaction?

A) I
B) II
C) III
D) IV

54) What is the IUPAC name of the following compound?

A) 5-Ethylthio-4-isopropylpentane
B) 1-Ethylthio-3-methyl-2-propylbutane
C) 1-Ethylthio-2-isopropylpentane
D) Isooctylthioethane

55) What is the IUPAC name of the following compound?

A) 3-Ethyl-5-methylcyclohexanethiol
B) 3-Ethyl-5-methylcyclohexane-1-thiol
C) 5-Ethyl-2-methylcyclohexanethiol
D) 5-Ethyl-2-methylcyclohexylthiol

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56) What is the IUPAC name of the following compound?

A) (2R, 4R)-4-chloro-2-pentanol
B) (2R, 4S)-4-chloro-2-pentanol
C) (2S, 4R)-4-chloro-2-pentanol
D) (2S, 4S)-4-chloro-2-pentanol

57) What is the IUPAC name of the following compound?

A) R-2,2-dimethylcyclohexanol
B) S-2,2-dimethylcyclohexanol
C) R-1,1-dimethyl-2-cyclohexanol
D) S-1,1-dimethyl-2-cyclohexanol

58) What is the IUPAC name of the following compound?

A) R-2-methoxy-5,5-dimethylhexane
B) S-2-methoxy-5,5-dimethylhexane
C) R-5-methoxy-2,2-dimethylhexane
D) S-5-methoxy-2,2-dimethylhexane

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59) What is the major product of the following reaction?

A) I
B) II
C) III
D) IV

60) What is the major product of the following reaction?

A) I
B) II
C) III
D) IV

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