Chapter 08 Merged
Chapter 08 Merged
Chapter 08 Merged
MULTIPLE CHOICE
2. Which of the following molecules is the correct structure for dibenzyl ether?
A)
B)
C)
D)
E)
A) 2-bromo-4-ethyl-4-methoxypentane
B) 4-bromo-2-ethyl-2-methoxypentane
C) 2-bromo-4-methoxy-4-methylhexane
D) 2-bromo-3-methoxy-3-methylhexane
E) ethyl methyl propyl ether
ANS: C TOP: Structure and Nomenclature of Ethers
4. Which of the following molecules is named oxirane?
A)
B)
C)
D)
E)
A) 1,2-dimethyloxirane
B) trans-1,2-dimethyloxirane
C) 2-butene oxide
D) cis-1,2-dimethyloxirane
E) oxobutane
ANS: B TOP: Structure and Nomenclature of Ethers
C)
D)
E)
ANS: B TOP: Structure and Nomenclature of Ethers
A) 3-ethoxy-3-methylpropane
B) ethyl isobutyl ether
C) butyl ethyl ether
D) 2-ethoxybutane
E) 3-ethoxybutane
ANS: D TOP: Structure and Nomenclature of Ethers
A) [8]crown-4
B) [12]crown-4
C) [4]crown-4
D) [15]crown-5
E) [18]crown-6
ANS: B TOP: Structure and Nomenclature of Ethers
B)
C)
D)
E)
11. Which one of the following molecules has the highest boiling point?
A) 3-methoxy-1-propanol
B) 1,2-dimethoxyethane
C) 1,4-butanediol
D) 1,1-dimethoxyethane
E) 2-methoxy-1-propanol
ANS: C TOP: Properties of Ethers
14. Starting with p-bromoanisole (p-bromophenyl methyl ether), what sequence of reactions will
produce p-deuterioanisole?
A)
B)
C)
D)
E)
16. The synthesis of dipropyl ether can be accomplished using 1-propanol. What reactants and
conditions are necessary for this to occur?
A) Na and 180°
B) PBr3 and 140°
C) H2SO4 and 140°
D) Zn and H+
E) PCC and 180°
ANS: C TOP: Preparation of Ethers
17. The best Williamson synthesis of cyclohexyl methyl ether involves the following reaction:
A)
B)
C)
D)
E)
18. What alkene reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl
ether?
A) ethylene
B) 2-methylpropene
C) 2-butene
D) propene
E) 1-butene
ANS: B TOP: Preparation of Ethers
B)
C)
D)
E)
20. When anisole (methyl phenyl ether) is treated with concentrated HBr, which of the following
products are produced?
A) I
B) II
C) III
D) IV
E) I and IV
ANS: D TOP: Preparation of Ethers
22. Which of the following ethers will cleave the fastest with H2O and H+?
A)
B)
C)
D)
E)
B)
C)
D)
E)
ANS: D TOP: Preparation of Ethers
are:
A) ethanol and iodobenzene.
B) ethyl iodide and iodobenzene.
C) ethanol and phenol.
D) ethyl iodide and phenol.
E) ethylene oxide and phenol.
ANS: D TOP: Preparation of Ethers
B)
C)
D)
E)
26. The first step in the mechanism of acid catalyzed ring opening of oxirane is:
A) protonation of the oxygen in the oxirane.
B) anion attack of the carbon in the oxirane.
C) cation attack of the carbon in the oxirane.
D) formation of a stable carbocation.
E) none of the above.
ANS: A TOP: Preparation and Reactions of Epoxides
27. When cyclopentene is treated with peroxyacetic acid, the product that forms is:
A) 1,2-cyclopentanediol
B) 1,2-pentanediol
C) pentanol
D) cyclopentene oxide
E) dicyclopentyl ether
ANS: D TOP: Preparation and Reactions of Epoxides
28. The correct structure for peroxyacetic acid is:
A)
B)
C)
D)
E)
A) D)
B) E)
C)
A) NaOH
B) CH3CO3H
C) H2O, H2SO4
D) (a) BH3 (b) NaOH, H2O2
E) CH3CO2H
ANS: B TOP: Preparation and Reactions of Epoxides
A) CH3CH2CH2CH3.
B) CH3CH2OCH2CH2OH.
C) CH3CH2OCH2CH2OCH2CH3.
D) CH3CH2OCH2CH2CH2OH.
E) none of the above.
F) all of the above.
ANS: B TOP: Preparation and Reactions of Epoxides
A)
B)
C)
D)
E) none of these
ANS: C TOP: Miscellaneous
35. 1 mole of bromocyclohexane reacts with 2 moles of Li to give:
A) cyclohexene
B) cyclohexyllithium
C) cyclohexane
D) hexane
E) hexyllithium
ANS: B TOP: Miscellaneous
38. Adding Br2 in H2O will distinguish which of following pairs of compounds?
A) diisopropyl ether and hexane
B) ethyl phenyl ether and allyl phenyl ether
C) 1-butanol and methyl propyl ether
D) diethyl ether and ethanol
E) toluene and anisole
ANS: B TOP: Miscellaneous
Chapter 7 -- Alcohols, Phenols & Thiols
MULTIPLE CHOICE
A) I
B) II
C) III
D) IV
E) V
ANS: C TOP: Nomenclature of Alcohols
B)
C)
D)
E)
A) 2-methyl-4-pentanol
B) 2-methyl-4-hydroxypentane
C) 4-methyl-2-pentanol
D) 4-hydroxy-2-methylpentane
E) 2-hydroxy-4-methylpentane
ANS: C TOP: Nomenclature of Alcohols
A) I
B) II
C) III
D) IV
E) V
ANS: D TOP: Nomenclature of Alcohols
A) 2-pentanol
B) 3-thiopentanol
C) 2-pentanethiol
D) 4-pentanethiol
E) pentylsulfide
ANS: C TOP: Nomenclature of Alcohols
A) 1-ethyl-2-methylbenzyl alcohol
B) methylphenylpropanol
C) 2-methyl-2-phenyl-1-propanol
D) 2-phenyl-2-butanol
ANS: D TOP: Nomenclature of Alcohols
A) 2-hydroxybromobenzene.
B) 2-bromobenzyl alcohol.
C) 2-bromobenzol.
D) o-bromophenol.
E) 2-bromohexanol
ANS: D TOP: Nomenclature of Alcohols
B)
C)
D)
E)
11. Which of the following molecules would be the best hydrogen bond donor?
A) CH3CH2OCH3
B) CH3CN
C) CH3OH
D) CH3SH
E) CH3CH2NH2
ANS: C TOP: Properties of Alcohols
12. Which of the following molecules would have the highest boiling point?
A) CH3CH2OH
B) CH3OCH3
C) CH3CH2Cl
D) CH3CH2CH3
E) CH3CH2I
ANS: A TOP: Properties of Alcohols
A) 3>2>1
B) 1>2>3
C) 1>3>2
D) 2>3>1
E) 2>1>3
ANS: D TOP: Properties of Alcohols
16. If the pKa of isopropyl alcohol is 17, what is the Ka of isopropyl alcohol?
A) 17 10–17
B) 10–17
C) 10–3
D) 1017
E) 103
F) 17 1017
ANS: B TOP: Acid-Base Chemistry
17. Which of the following molecules would be the strongest Brønsted-Lowry acid?
A) H2O
B) CH4
C) HF
D) HCl
E) NH3
ANS: D TOP: Acid-Base Chemistry
B) E)
C)
B)
C)
D)
E)
23. Which of the following alcohols would react most rapidly under SN1 conditions?
A) CH3OH
B) CH3CH2OH
C) (CH3)2CHCH2OH
D) (CH3)3COH
E) CH3CH2CH2OH
ANS: D TOP: Reaction Mechanisms
27. What type of compound is formed when a secondary (2°) alcohol is treated with Jones'
reagent?
A) an alkene
B) an alkyne
C) an aldehyde
D) a ketone
E) a carboxylic acid
ANS: D TOP: Reactions
28. When an alcohol reacts with an alkali metal like Na, the product formed is a(n):
A) alkene
B) alkoxide
C) acetylide
D) alkane
E) hydroxide
F) alkyne
ANS: B TOP: Reactions
29. Which reagents would you use to accomplish the following transformation?
A) I
B) II
C) III
D) IV
E) II and IV
ANS: E TOP: Reactions
A) 1. PCl3 2. H3O+
B) CrO , H in acetone
3
C) PCC, CH2Cl2
D) 1. Na 2. CH3OH
E) none of the above
ANS: C TOP: Reactions
33. Acid-catalyzed dehydration of 3-methyl-3-hexanol can give the following number of alkenes
(including stereoisomers):
A) 2
B) 3
C) 4
D) 5
E) 6
ANS: D TOP: Reactions
35. Oxidation of secondary alcohols with Jones' reagent (CrO3, H+, acetone) gives
A) carboxylic acids.
B) aldehydes.
C) ketones.
D) chromate esters.
E) tertiary alcohols.
ANS: C TOP: Reactions
36. Which of the following reagents will oxidize primary alcohols to carboxylic acids?
1. CrO3, H2SO4
2. PCC
3. PCl3
4. SOCl2
A) only 1
B) only 2
C) only 3
D) only 4
E) 1 and 2
ANS: A TOP: Reactions
37. Which of the following reagents will oxidize secondary alcohols to ketones?
1. CrO3, H2SO4
2. PCC
3. PCl3
4. SOCl2
A) only 1
B) only 2
C) only 3
D) only 4
E) 1 and 2
ANS: E TOP: Reactions
39. Which reagent or reagents can be used irreversibly to accomplish the following
transformation:
1. NaH
2. Na
3. NaOH
A) only 1
B) only 2
C) only 3
D) 1 and 2
E) 1, 2, and 3
ANS: D TOP: Reactions
A) pyridinium chlorochromate
B) K2Cr2O7, H2SO4, H2O
C) H2O2, NaOH, H2O
D) Ag(NH3)2+, NaOH (Tollen's reagent)
E) all of the above
ANS: B TOP: Reactions
A) CH3CH2CH2CH2SCH3
B) CH3CH2CH2CH2OCH3
C) (CH3CH2CH2CH2S)2
D) CH3CH2CH2CH2OH
ANS: A TOP: Reactions
A) CH3CH2CH=CH2
B) cis-CH3CH=CHCH3
C) trans-CH3CH=CHCH3
D) (CH3)2C=CH2
Chapter 12: Alcohols, Phenols, Thiols, and Ethers
1. What class of compounds is represented by the general formula RSH?
A) alcohols
B) ethers
C) thiols
D) phenols
E) disulfides
Ans: C
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5. The IUPAC name for the compound shown below is 1,2,3-propanetriol. What is the
common name of this compound?
A) glycerol
B) ethylene glycol
C) phenol
D) isopropyl alcohol
E) menthol
Ans: A
A) 1-propanol
B) 1-cyclopentanol
C) cyclopropanol
D) phenol
E) glycerol
Ans: C
7. Which of the following statements about the compound shown below is FALSE?
A) It is a tertiary alcohol.
B) Its name is 2-methyl-3-pentanol.
C) It can participate in hydrogen bonding.
D) It can be oxidized to a ketone.
E) It contains both a nonpolar and a polar region.
Ans: A
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
A)
B)
C)
D)
E)
Ans: B
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
10. When methanal, the simplest aldehyde, undergoes reduction by the addition of
hydrogen, what product results?
A) methanol
B) methane
C) methanone
D) formaldehyde
E) carbon dioxide
Ans: A
11. Which of the following is NOT a possible alkene product from the dehydration reaction
of 2-butanol?
A)
B)
C)
D)
E) All of the above alkenes are possible products.
Ans: C
A) substitution
B) oxidation
C) addition
D) reduction
E) condensation
Ans: B
13. Which product of the oxidation of ethanol causes many of the symptoms of the
“morning-after hangover”?
A) phenol
B) resveratrol
C) ethanal
D) formaldehyde
E) ethylene glycol
Ans: C
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
14. What is the most common use of phenol derivatives in health care?
A) antiseptics/disinfectants
B) antibiotics
C) anesthetics
D) radiation therapy
E) suture material
Ans: A
16. What is the typical medical use for the compounds shown below?
A) antiseptics/disinfectants
B) antibiotics
C) anesthetics
D) radiation therapy
E) suture material
Ans: C
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
B)
C)
D)
E)
Ans: A
18. Which of the following is the structure for methyl tertiary butyl ether?
A)
B)
C)
D)
E)
Ans: A
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
19. Which class of compounds is primarily responsible for the foul smell of skunk spray?
A) phenols
B) thiols
C) diols
D) acetals
E) ketones
Ans: B
20. What important type of bond, formed between two sulfhydryl (-SH) groups, plays a key
role in the shapes of many proteins?
A) cysteine bond
B) hydrogen bond
C) disulfide bond
D) thioester bond
E) double bond
Ans: C
21. What role does the thiol coenzyme A perform in biochemical reactions?
A) It serves as the energy source for energy-requiring reactions.
B) It serves as a carrier of two-carbon acetyl groups.
C) It serves as an identification marker on the surface of cells.
D) It functions as a catalyst for reduction reactions.
E) It is a structural component of muscle and bone.
Ans: B
24. What is the name of the alcohol produced by the fermentation of sugars and starches,
and contained in alcoholic beverages?
A) methyl alcohol D) propanol
B) isopropyl alcohol E) ethanol
C) methanol
Ans: E
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
A) primary D) quaternary
B) secondary E) phenol
C) tertiary
Ans: C
26. What is the name of the product formed in the following reaction, the catalyzed
hydrogenation of 2-butanone?
A) butane D) butanol
B) isobutyl alcohol E) butanal
C) 2-butanol
Ans: C
28. Which type of alcohol does NOT undergo oxidation under normal conditions?
A) primary D) Both B and C are correct.
B) secondary E) All alcohols undergo oxidation.
C) tertiary
Ans: C
29. Which statement best describes the solubility of the alcohol whose structure is shown
below?
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
B)
C)
D)
C)
Ans: C
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
33. Dehydration of the alcohol shown below produces styrene, an important starting
material in the polymer and plastics industry. What is the structure of styrene?
A)
B)
C)
D)
E)
Ans: B
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
35. Although ethanol is fit for human consumption, methanol is quite toxic if ingested. The
toxicity is due to the aldehyde produced when methanol is oxidized in the liver. Which
of the following is the aldehyde formed by the oxidation of methanol?
A)
B)
C)
D)
E)
Ans: E
A) 2-methyl-3-hexanol D) 2-methyl-3-pentanol
B) 5-methyl-4-hexanol E) 2,2-dimethyl-3-pentanol
C) 3-methyl-2-hexanol
Ans: C
A)
B)
C)
D)
E)
Ans: A
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
38. Ethylene glycol is the common name for the compound with the structure:
HOCH2CH2OH. What is the IUPAC name for this compound?
A) 1,2-diethanol
B) 1,2-phenol
C) propanol
D) dihydroxyethane
E) 1,2-ethanediol
Ans: E
39. What alcohol can cause blindness and possibly death when it is consumed?
A) ethanal B) ethanol C) methanal D) methanol E) 1,2,3-propanetriol
Ans: D
40. Zaitsev’s rule can be used to predict the major alkene product in a dehydration reaction.
Which of the following alkenes would be the major product of the dehydration reaction
shown below?
A)
B)
C)
D)
E) All are equally likely.
Ans: B
42. What is the name of the product of the reaction below, which requires acid as a catalyst?
CH2=CH2 + H2O → ?
A) ethanol B) ethanal C) methanal D) methanol E) 1,2,3-propanetriol
Ans: A
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
44. What type of compound is produced by the reduction of aldehydes and ketones?
A) alkene B) phenol C) alkane D) carboxylic acid E) alcohol
Ans: E
45. When an alcohol is heated with concentrated sulfuric acid (H2SO4), which of the
following reaction types is likely to occur?
A) hydration D) oxidation
B) dehydration E) substitution
C) dehydrogenation
Ans: B
46. The hydration reaction below follows Markovnikov’s rule. Which of the following is
the expected major product of this reaction?
A)
B)
C)
D)
E)
Ans: C
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
48. The condensation reaction between the two alcohols below produces what type of
compound?
49. Which one of the following biochemical species contains a thioester bond which plays a
key role in its function?
A) NAD+ B) NADH C) DNA D) acetyl CoA E) ADP
Ans: D
A)
B)
C)
D)
51. Which of the following compounds has the highest boiling point?
A) CH2(OH)CH(OH)CH2OH (molar mass = 92 g/mol)
B) CH2(OH)CH2CH2CH2OH (molar mass = 90 g/mol)
C) CH3CH2CH2CH2CH2OH (molar mass = 88 g/mol)
D) CH3CH(OH)CH2CH2OH (molar mass = 90 g/mol)
E) CH3CH2CH2CH2CH2CH3 (molar mass = 86 g/mol)
Ans: A
52. Which statement best explains why alcohols have a higher boiling point than alkanes
with a similar molar mass?
A) Alcohols have weaker intermolecular forces than alkanes.
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
B) Alcohols have London forces only and alkanes have dipole-dipole attractions.
C) Alcohols have strong hydrogen bonding forces between molecules and alkanes
have weaker London forces.
D) Alcohols have stronger London forces than alkanes.
E) None of the choices are correct.
Ans: C
A) 5-chloro-4-hexanol D) 3-chloro-4-butanol
B) 2-chloro-3-hexanol E) 1-chloro-1-methyl-2-pentanol
C) 1-ethylchloro-butanol
Ans: B
54. Which of the following is expected to have the greatest solubility in water?
A) CH3OH D) CH3CH3
B) CH3CH2CH2CH2OH E) Both A and D are equally soluble.
C) CH3CH2CH2CH2CH3
Ans: A
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
59. Lactic acid gives sour milk its distinctive taste. What product is formed when lactic
acid is oxidized?
A)
B)
C)
D)
E)
Ans: D
61. A primary alcohol has two alkyl groups attached to the carbinol carbon.
Ans: False
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Chapter 12 Alcohols, Phenols, Thiols, and Ethers
64. Oxidation may be classified as the gain of bonds to oxygen, or the loss of bonds to
hydrogen.
Ans: True
65. Stepwise oxidation of a primary alcohol produces first an ether and then a carboxylic
acid.
Ans: False
67. A phenol is a compound that contains a hydroxyl group attached to a benzene ring.
Ans: True
69. The formation of a disulfide bond (-S-S-) between two sulfhydryl groups (-SH) is an
oxidation process.
Ans: True
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