CHEM 121 Chapter 14. Name: __________________________ Date: _____________ 1. The simplest alcohol, from a structural standpoint, contains how many carbon atoms and how many oxygen atoms? A) one carbon atom and one oxygen atom B) one carbon atom and two oxygen atoms C) two carbon atoms and one oxygen atom D) two carbon atoms and two oxygen atoms CH3 CH

2. The correct IUPAC name for A) isopropyl alcohol. B) 2-methyl ethanol. C) 2-propanol. D) hydroxypropane. CH3

3. The correct IUPAC name for A) hexyl dialcohol. B) 2,6-dihydroxyhexane. C) 2,6-hexanediol. D) 1,5-hexanediol.

OH

CH3

is

CH

CH2 CH2

OH

CH2

CH2 OH is

4. Which of the following statements concerning common alcohols is correct? A) wood alcohol and grain alcohol are one and the same B) rubbing alcohol is pure methyl alcohol C) absolute alcohol is pure methanol D) absolute ethanol has all water removed from it 5. In which of the following pairs of alcohols do both members of the pair contain two or more hydroxyl groups? A) s-butanol and ethylene glycol B) propylene glycol and glycerol C) t-butyl alcohol and ethylene glycol D) propanol alcohol and t-butanol alcohol

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6. Alcohols have higher boiling points than alkanes of similar molecular mass because A) alcohols are ionic compounds and alkanes are covalent compounds. B) alkane molecules are polar and alcohol molecules are not. C) hydrogen bonding occurs between alcohol molecules but not between alkane molecules. D) alcohols are acidic and alkanes are not. 7. How many hydrogen bonds can form between an isopropyl molecule and other isopropanol molecules? A) one B) two C) three D) four 8. A general method for preparing alcohols is the A) hydration of alkenes. B) combustion of alkanes. C) combustion of ethers. D) hydrogenation of alkenes. 9. Which of the following is a secondary alcohol? A) B)

C)

D)

10. Intramolecular dehydration of an alcohol produces a(n) A) alkane. B) alkene. C) ether. D) thiol.

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11. Oxidation of a secondary alochol produces a(n) A) ketone B) aldehyde C) carboxylic acid D) ether 12. Which of the following statements concerning phenols is incorrect? A) phenols are flammable B) they easily dissolve in water C) they are easily oxidized and therefore used as antioxidants D) unlike alcohols they are weak acids in solution

13. The correct IUPAC name for A) 1,4-diiodophenol B) 2,4-diiodophenol C) 2,5-diiodophenol D) 1,5-diiodophenol

is

14. All of the following general formulas except one represent an ether. The exception is A) R-O-R B) Ar-O-R C) H-O-Ar D) Ar-O-Ar 15. What is the IUPAC name for the ether whose common name is ethyl phenyl ether? A) 1-ethoxybenzene B) 2-ethoxybenzene C) 1-phenoxyethane D) 2-phenoxyethane 16. In chemical reactivity, ethers resemble A) alkanes. B) alkenes. C) alcohols. D) phenols.

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17. The sulfhydryl functional group is found in A) thiols. B) disulfides. C) both thiols and disulfides. D) neither thiols nor disulfides. 18. Which of the following is the structure for 1-propanethiol? A)

B)

C) D)

19. Which of the following molecules contains both an alkoxy group and a hydroxy group? A) B) C) D) 20. In which of the following pairs of compounds are the two members of the pair constitutional isomers? A) methoxymethane and ethoxyethane B) pentanol and pentanediol C) propyl alcohol and dipropyl ether D) isobutyl alcohol and diethyl ether 21. In which of the following pairs of names do both names represent the same alcohol? A) 2-propanol and propyl alcohol B) 1-propanol and isopropyl alcohol C) 2-methyl-2-propanol and isobutyl alcohol D) more than one correct response E) no correct response

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22. Which of the following is a correct name-composition pairing for an alcohol? A) 2-methylpentanol; 6 carbon atoms and 2 OH groups B) ethylene glycol; 3 carbon atoms and 2 OH groups C) glycerol; 3 carbon atoms and 3 OH groups D) more than one correct response E) no correct response 23. The solubility of alcohols in water A) decreases as the carbon chain length increases. B) decreases as the number of –OH groups present increases. C) increases with increasing molecular mass. D) more than one correct response E) no correct response 24. In a secondary alcohol, the hydroxyl-bearing carbon atom A) is always involved in a double bond. B) is attached to two other carbon atoms. C) cannot be bonded to hydrogen atoms. D) more than one correct response E) no correct response 25. Which of the following conditions for an alcohol dehydration reaction with H2SO4 as the catalyst will produce an ether? A) 1º alcohol, 180ºC B) 2º alcohol, 140ºC C) 1º alcohol, 140ºC D) more than one correct response E) no correct response 26. For which of the following intramolecular alcohol dehydrations is Saytzeff's rule needed to predict the structure of the alkene formed in the greatest amount? A) 1-propanol B) 2-propanol C) 1-butanol D) more than one correct response E) no correct response

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27. For which of the following alcohol oxidations is the listed oxidation product incorrect? A) primary alcohol; aldehyde B) secondary alcohol; ketone C) tertiary alcohol; carboxylic acid D) more than one correct response E) no correct response 28. Which of the following is an incorrect IUPAC name for a phenol derivative? A) 1-chlorophenol B) 2,5-dibromophenol C) 3-methylphenol D) more than one correct response E) no correct response 29. Ethers may be viewed as derivatives of water in which both hydrogen atoms have been replaced with A) hydrocarbon groups. B) hydroxyl groups. C) alkoxy groups. D) more than one correct response E) no correct response 30. In which of the following pairs of names do both names represent the same ether? A) diethyl ether and 1,2-diethoxyethane B) methyl isopropyl ether and 1-methoxypropane C) ethyl isopropyl ether and 2-ethoxypropane D) more than one correct response E) no correct response 31. Which of the following is a characteristic property of thiols? A) extremely strong odors B) abnormally high boiling points C) strong resistance to oxidation D) more than one correct response E) no correct response

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32. Which of the following pairings of names and general formulas is incorrect? A) dithiol and HS–R–SH B) thioether and R–S–R C) disulfide and R–S–S–R D) more than one correct response E) no correct response 33. Which of the following general types of compounds is always a heterocyclic compound? A) a substituted phenol B) a cyclic ether C) a cyclic compound with both hydroxy and alkoxy substituents on the ring D) more than one correct response E) no correct response 34. Which of the following compounds contains two oxygen atoms? A) 1,3-dimethoxybenzene B) methoxycyclohexane C) 2-ethoxy-1-propanol D) more than one correct response E) no correct response 35. Which of the following compounds is not a constitutional isomer of 1-butanol? A) diethyl ether B) 2-methyl-2-propanol C) 2-methoxypropane D) more than one correct response E) no correct response Use the following to answer questions 36-45: In each of the following multiple-choice questions characterize EACH of the three given statements as being TRUE or FALSE and then indicate the collective true-false status of the statements using the choices a) All three statements are true. b) Two of the three statements are true. c) Only one of the statements is true. d) None of the statements is true.

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36. Statements: (1) Common names for alcohols have two words and IUPAC names for alcohols are only one word. (2) Mild oxidizing agents readily oxidize tertiary alcohols. (3) Cyclic ethers are examples of heterocyclic organic compounds. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 37. Statements: (1) Long-chain alcohols are generally more soluble in water than short-chain alcohols. (2) The compound ethyl methyl ether contains two alkoxy groups. (3) Rubbing alcohol is a 50-50 mixture by volume of isopropyl alcohol and water. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 38. Statements: (1) Glycerin, a three-carbon diol, has a great affinity for moisture (water vapor). (2) Oxidation of a thiol produces a disulfide. (3) MTBE is a water-soluble polymeric alcohol. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 39. Statements: (1) Denatured alcohol is ethyl alcohol that has been rendered unfit to drink. (2) The functional group present in the compound 2-butanethiol is the sulfhydryl group. (3) The simplest phenol, phenol itself, is a colorless solid with a medicinal odor. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true.

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40. Statements: (1) Alcohols have higher boiling points than alkanes of similar molecular mass because of hydrogen bonding. (2) Ethylene glycol contains two carbon atoms and two hydroxyl groups. (3) Primary and secondary alcohols give the same type of product when subjected to mild oxidizing agents. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 41. Statements: (1) Intramolecular alcohol dehydration converts an alcohol to an alkene. (2) An aryl group is an aromatic carbon-ring system from which one hydrogen atom has been removed. (3) Unlike alcohols, phenols are weak acids in solution. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 42. Statements: (1) Propyl alcohol and methoxyethane are constitutional isomers. (2) Zaitsev's rule is used in predicting the major organic product from intermolecular alcohol dehydration. (3) An older name for methyl alcohol is grain alcohol. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 43. Statements: (1) 2-propanol is a secondary alcohol. (2) Each of the three methylphenols has a different common name. (3) The compound 4-methoxy-2-butanol is both an alcohol and an ether. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true.

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44. Statements: (1) Isopropyl alcohol and 1-propanol are two names for the same compound. (2) Ether molecules cannot hydrogen bond to one another. (3) Alcohol molecules have both polar and nonpolar character. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. 45. Statements: (1) Menthol is a naturally occurring terpene alcohol with a minty odor. (2) THC, the active ingredient in marijuana, contains phenol, cyclic ether and halogen functional groups. (3) Ether-type anesthetics in use today are usually halogenated compounds. A) All three statements are true. B) Two of the three statements are true. C) Only one of the statements is true. D) None of the statements is true. Use the following to answer questions 46-50: For each of the hydrocarbon derivatives, select from the response list the correct molecular formula. Responses may be used more than once or need not be used at all. a) C4H10O b) C4H12O c) C4H10O2 d) C4H12O2 46. Ethoxyethane 47. Tertiary-butyl alcohol 48. 1,3-Butanediol 49. 1,2-Dimethoxyethane 50. 2-Methyl-1-propanol

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Use the following to answer questions 51-55: Match the alcohol characteristics with names in the response list. Responses may be used more than once or need not be used at all. a) drinking alcohol b) rubbing alcohol c) glycerin d) ethylene glycol 51. Contains 2 –OH groups 52. Contains isopropyl alcohol 53. Contains 3 –OH groups 54. Contains 2 carbons and 1 –OH group 55. Obtained from fermentation of grain products Use the following to answer questions 56-60: Match the structural formulas with compound types in the response list. Responses may be used more than once or need not be used at all. a) thioether b) disulfide c) diol d) thiol 56. CH3–S–S–CH 57. HO–CH2–CH2–OH 58. CH3–S–CH3 59. CH3–CH2–SH 60. CH3–CH2–S–CH3

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Use the following to answer questions 61-65: For each pair of compounds, select a correct structural characterization from the response list. Responses may be used more than once or need not be used at all. a) are constitutional isomers b) have the same number of carbon atoms and same number of oxygen atoms but are not constitutional isomers c) have the same number of carbon atoms but a different number of oxygen atoms d) have the same number of oxygen atoms but a different number of carbon atoms

61. 1-Butanol 2-Butanol 62. 1-Methoxypropane Ethoxyethane 63. 3-Chlorophenol o-Cresol 64. Cyclohexanol Phenol 65. 1,3-Butanediol Methyl isopropyl ether Use the following to answer questions 66-70: For each set of reactants, select a correct product characterization from the response list. Responses may be used more than once or need not be used at all. a) alkene b) aldehyde c) ether d) ketone 66. Primary alcohol Sulfuric acid 180ºC 67. Secondary alcohol Sulfuric acid 180ºC 68. Secondary alcohol Sulfuric acid 140ºC 69. Primary alcohol Mild oxidizing agent

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70. Secondary alcohol Mild oxidizing agent

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Answer Key 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 39. 40. 41. 42. 43. 44.

A C D D B C C A C B A B C C A A A C C D C C A B C E C D A C A E B D E B D C A B A C B B

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45. 46. 47. 48. 49. 50. 51. 52. 53. 54. 55. 56. 57. 58. 59. 60. 61. 62. 63. 64. 65. 66. 67. 68. 69. 70.

B a a c c a d b c a a b c a d a a a d b c a a a b d

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