CHEM 121. Chapter 15 Name: Date:

CHEM 121. Chapter 15 Name: Date: 1. Which of the following structural features is common to both aldehydes and ketones? A) B) C) D) 2. Which of the following structural features is possessed by aldehydes but not ketones? A) At least one hydrogen atom is bonded to the carbonyl carbon atom. B) At least one hydroxyl group is bonded to the carbonyl carbon atom. C) The carbonyl carbon atom is bonded to two other carbon atoms. D) The carbonyl carbon atom is part of a ring structure. 3. Which of the following statements concerning aldehydes and ketones is correct? A) cyclic aldehydes exist B) cyclic ketones exist C) both cyclic aldehydes and cyclic ketones exist D) neither cyclic ketones nor cyclic aldehydes exist 4. The simplest aldehyde and ketone contain, respectively, how many carbon atoms? A) 1 and 1 B) 1 and 3 C) 2 and 2 D) 2 and 3 Page 1

5. The IUPAC name for the compound CH 3 CH 2 C H is A) acetaldehyde. B) propionaldehyde. C) 1-ethanal. D) propanal. O 6. The IUPAC name for the compound CH 3 C A) 2-methyl-2-pentanone. B) 2-methyl-4-pentanone. C) 4-methyl-2-pentanone. D) 2-methyl-4-pentaketone. O CH 2 CH 3 CH CH3 is 7. What is the IUPAC name of the aldehyde whose common name is propionaldehyde? A) propanal B) methanal C) ethanal D) 2-methylbutanal 8. Two other acceptable names for the compound acetone are A) propanone and diethyl ketone. B) ethanone and methyl ethyl ketone. C) propanone and dimethyl ketone. D) ethanone and diethyl ketone. 9. How many saturated noncyclic six-carbon ketones are there? A) two B) four C) six D) eight 10. What two functional groups are never found at the end of a carbon chain? A) alcohol and aldehyde B) ether and aldehyde C) alcohol and ketone D) ether and ketone Page 2

11. Which of the following statements concerning hydrogen bonding is correct? A) ketone molecules can hydrogen bond to each other B) aldehyde molecules can hydrogen bond only to other aldehyde molecules C) both ketone molecules and aldehyde molecules can hydrogen bond to each other D) aldehyde molecules cannot hydrogen bond to other aldehyde molecules 12. Comparison of the boiling points of aldehydes and ketones with those of other compounds of similar molecular mass shows that they are A) lower than those of alkanes and alcohols B) higher than those of alcohols and alkanes C) higher than those of alcohols but lower than those of alkanes D) higher than those of alkanes 13. Which of the following statements concerning the oxidation of aldehydes and ketones is correct? A) ketones are resitant to oxidation and aldehydes readily undergo oxidation B) ketones readily undergo oxidation C) both aldehydes and ketones readily undergo oxidation D) both aldehydes and ketones are resistant to oxidation 14. Which of the following statements concerning the oxidation of aldehydes and ketones is correct? A) Aldehydes readily undergo oxidation and ketones are resistant to oxidation. B) Ketones readily undergo oxidation and aldehydes are resistant to oxidation. C) Both aldehydes and ketones readily undergo oxidation. D) Both aldehydes and ketones are resistant to oxidation. 15. The oxidizing agent in the Tollen's test for the presence of an aldehyde is A) Ag + B) Ag C) Cu 2+ D) Cu2O Page 3

16. What is the product when CH 3 C A) O CH 3 is reduced using H2 gas and a Ni catalyst? B) C) D) 17. When an alcohol molecule adds across a carbon-oxygen double bond of an aldehyde or ketone, the A) H atom from the alcohol bonds to the carbonyl carbon atom. B) OH portion from the alcohol bonds to the carbonyl oxygen atom. C) OR portion from the alcohol bonds to the carbonyl carbon atom. D) OH portion from the alcohol bonds to the carbonyl carbon atom. 18. A hemiacetal is a compound in which A) a hydroxy group and an alkoxy group are attached to the same carbon atom. B) a hydroxyl group and an alkoxy group are attached to adjacent carbon atoms. C) two alkoxy groups are attached to the same carbon atom. D) two alkoxy groups are attached to adjacent carbon atoms. 19. The structural difference between a hemiacetal and an acetal is the replacement of a A) OH group with an OR group. B) H atom with an OR group. C) H atom with a OH group. D) OR group with a OH group. 20. Hydrolysis of an acetal in an acid solution would yield A) an aldehyde, a ketone, and one alcohol. B) an aldehyde, a ketone, and two alcohols. C) an aldehyde or a ketone and one alcohol. D) an aldehyde or a ketone and two alcohols. Page 4

21. Which of the following statements concerning a carbonyl group is incorrect? A) It is polar. B) It contains two oxygen atoms and one carbon atom. C) It is present in both aldehydes and ketones. 22. Which of the following is a correct notation for the aldehyde functional group? A) B) C) 23. Which of the following aldehydes is paired with an incorrect IUPAC name? A) B) C) 24. Which of the following pairings of aldehyde common and IUPAC names is correct? A) acetaldehyde and methanal B) 2-methylbutyraldehyde and 2-methylbutanal C) formaldehyde and ethanal Page 5

25. Which of the following pairings of ketone IUPAC and common names is correct? A) 2-methyl-3-pentanone and methyl propyl ketone B) 3-methyl-2-pentanone and isopropyl methyl ketone C) propanone and dimethyl ketone 26. Which of the following compounds is a constitutional isomer of 2-pentanone? A) 3-methyl-2-pentanone B) 3-methyl-2-butanone C) isopropyl methyl ketone 27. Which of the following compounds contains 7 carbon atoms? A) benzaldehyde B) acetophenone C) benzophenone 28. In which of the following pairs of compounds does the first listed compound have a greater water solubility than the second listed compound? A) butanal, methanal B) propanone, 2-pentanone C) hexanal, 2-butanone 29. Oxidation of which of the following alcohols will produce a ketone? A) B) C) Page 6

30. Which of the following compounds would be resistant to oxidation with a mild oxidizing agent? A) B) C) 31. Hydrogenation, with a catalyst, of which of the following compounds would produce a four-carbon alcohol? A) butanal B) 2-butanone C) diethylketone 32. In which of the following pairings of compound types does the first listed compound type contain more alkoxy groups than the second listed compound type? A) acetal, hemiacetal B) hemiacetal, acetal C) aldehyde, hemiacetal 33. Which of the following is a product of the acid hydrolysis of the following compound? OH CH 3 CH 2 C H O CH 3 A) methyl alcohol B) ethyl alcohol C) propanone Page 7

34. Which of the following types of compounds contains a carbon-sulfur double bond? A) a thial (thioaldehyde) B) a thione (thioketone) C) a sulfoxide 35. Which of the following compounds would be named as a ketone? A) B) C) 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. 36. Statements: (1) Cyclic hemiacetals are usually more stable than noncyclic hemiacetals. (2) A carbonyl group consists of a carbon atom and an oxygen atom joined by a double bond. (3) The compound benzaldehyde contain six carbon atoms. Page 8

37. Statements: (1) The simplest aldehyde is formaldehyde and the simplest ketone is acetone. (2) Carbonyl group polarity makes dipole-dipole interactions between like aldehyde molecules or like ketone molecules possible. (3) Reaction of a hemiacetal with an alcohol produces an acetal. 38. Statements: (1) Aldehydes and ketones readily undergo oxidation to carboxylic acids. (2) Propanone and dimethyl ketone are two names for the same compound. (3) The silver mirror test distinguishes between aldehydes and ketones. 39. Statements: (1) Acetals contain three oxygen atoms and hemiacetals contain two oxygen atoms. (2) Reduction of an aldehyde, using hydrogen gas, produces a primary alcohol. (3) In an aldehyde, the carbonyl group can be located on either carbon 1 or carbon 2. 40. Statements: (1) In a dial two aldehyde groups are present. (2) Formaldehyde readily participates in polymer formation. (3) Primary alcohol oxidation is a method for producing ketones. Page 9

41. Statements: (1) Butanal and 2-butanone are constitutional isomers. (2) The linear notation for an aldehyde is RCOH and that for a ketone is RCOR. (3) Water molecules can hydrogen bond with aldehyde and ketone molecules. 42. Statements: (1) The compound 4-oxopentanal contains both an aldehyde and an ether functional group. (2) An alkoxy group and a hydroxy group attached to the same carbon atom are present in both hemiacetals and acetals. (3) Cyclic aldehyde structures are possible but cyclic ketone structures are not possible. 43. Statements: (1) Butanal and butanone are both correct IUPAC names. (2) The two alcohol molecules produced when an acetal molecule undergoes hydrolysis are always identical. (3) Aldehydes and ketones are both classified as carbonyl-containing compounds. 44. Statements: (1) In the IUPAC nomenclature system, an aldehyde group has priority over a ketone group. (2) Addition of an alcohol molecule across the carbon-oxygen double bond of an aldehyde produces a compound in which the carbonyl carbon atom bears both an alkoxy group and a hydroxy group. (3) 2-Propenal contains two fewer hydrogen atoms than propionaldehyde. Page 10

45. Statements: (1) The lachrymator in wood smoke is formaldehyde. (2) The skin pigment melanin is a polymeric substance containing many interconnected aldehyde units. (3) Benedict's test can be used to detect glucose in urine (diabetes) because glucose contains an aldehyde group. Use the following to answer questions 46-50: Characterize each compound in terms of functional groups present using the response list. Responses may be used more than once or need not be used at all. a) one aldehyde functional group b) two aldehyde functional groups c) one ketone functional group d) one aldehyde and one ketone functional group 46. Pentanal 47. 3-Pentanone 48. Pentanedial 49. 3-Methylpentanone 50. 3-Oxopentanal Use the following to answer questions 51-55: For each pair of compounds, select a correct characterization from the response list. Responses may be used more than once or need not be used at all. a) have the same molecular formula but are different compounds b) both contain a carbon ring system c) contain the same number of carbon atoms but have different molecular formulas d) two names for the same compound Page 11

51. Acetone Propanal 52. Heptanal Benzaldehyde 53. Diethylketone Pentanal 54. Acetaldehyde Ethanal 55. 2,2-DimethylbutanaCyclohexanone Use the following to answer questions 56-60: For each of the compound characterizations, select from the response list the number of constitutional isomers that exist. Responses may be used more than once or need not be used at all. a) two b) three c) four d) five 56. Saturated four-carbon aldehyde 57. Saturated four-carbon monochloroaldehyde 58. Methylcyclohexanone 59. Saturated noncyclic five-carbon ketone 60. Molecular formula of C4H8O Page 12

Use the following to answer questions 61-66: 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) hemiacetal b) acetal c) alkene d) alcohol 61. Aldehyde Alcohol Acid catalyst 62. Ketone Two alcohols Acid catalyst 63. Hemiacetal Alcohol Acid catalyst 64. Aldehyde Hydrogen Ni catalyst 65. Ketone Hydrogen Ni catalyst 66. Oxidation of Use the following to answer questions 67-70: For each of the reaction types, select from the response list the type of organic compound produced. Responses may be used more than once or need not be used at all. O O OH O O R C H R C a) carboxylic acid b) ketone c) alcohol d) no reaction occurs R R CH R R C R R C H 67. Oxidation of 68. Oxidation of Page 13

69. Reduction of 70. Reduction of Page 14

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

45. B 46. a 47. c 48. b 49. c 50. d 51. a 52. c 53. a 54. d 55. c 56. a 57. d 58. b 59. b 60. b 61. a 62. b 63. b 64. d 65. d 66. a 67. d 68. b 69. c 70. c Page 16