upali/chem121/test/stoker-c16.docx · web viewwhich of the following compounds is a constitutional...

Name: __________________________ Date: _____________

1. The functional group present in carboxylic acids is called aA) carbonyl group.B) carboxyl group.C) carboxylate group.D) carbohydroxyl group.

2. Which of the following statements concerning the structure of the functional group present in carboxylic acids is incorrect?A) Two oxygen atoms are present.B) A carbon-oxygen single bond and a carbon-oxygen double bond are present.C) A carbon-hydrogen bond is present.D) An oxygen-hydrogen bond is present.

3.

The IUPAC name for the compound CH CH2 CCH3

CH3 O

OH isA) 2-methyl-4-butanoic acid.B) 2-methyl-4-pentanoic acid.C) 3-methylbutanoic acid.D) 3-methylpentanoic acid.

4. The common names for the C2 mono- and dicarboxylic acids are, respectively,A) formic acid and acetic acid.B) acetic acid and formic acid.C) oxalic acid and acetic acid.D) acetic acid and oxalic acid.

5. The common name for the C5 unbranched dicarboxylic acid isA) adipic acidB) glutaric acidC) pimelic acidD) succinic acid

6. Which of the following polyfunctional carboxylic acids is incorrectly characterized?A) tartaric acid, C4 dihydroxyacidB) malic acid, C4 hydroxyacidC) pyruvic acid, C3 ketoacidD) glyceric acid, C3 ketodiacid

7. Which of the following statements concerning the properties of carboxylic acids is incorrect?A) Short-chain monocarboxylic acids are liquids at room temperature.B) Carboxylic acids have higher boiling points than alcohols of similar molecular

mass.C) Carboxylic acids cannot hydrogen bond to water.D) Carboxylic acids can hydrogen bond to each other.

8. Carboxylic acids may be prepared by oxidation of eitherA) ketones or aldehydesB) secondary or primary alcoholsC) primary alcohols or aldehydesD) ketones or secondary alcohols

9. Which of the following statements concerning the acid strength of carboxylic acids is correct?A) all are weak acidsB) their acid strength is equal that of strong mineral acid such as HClC) aromatic acids are strong and nonaromatic acids are weakD) unbrached acids are strong

10. Which of the following statements concerning carboxylate ions is correct?A) they may be negatively or positively chargedB) carboxylate ions formed from dicarboxylic acids carry a -2 chargeC) they contain more carbon atoms than their parent acidsD) they are always positively charged

11. Carboxylic acid salts may be converted to their "parent" carboxylic acids by reacting them withA) a strong base such as NaOHB) a strong acid such as HIC) an alcohol such as methanolD) a ketone such as acetone

12. Which of the following acids would produce a carboxylate ion with a minus two charge?A)

B)

C)

D)

13. Which of the following is a general structural representation for an ester?A)

B)

C)

D)

14. Esters are produced through the reaction ofA) a ketone and an etherB) a carboxylic acid and an alcoholC) an aldehyde and a phenolD) a carboxylic acid and a ketone

15.

The IUPAC name for the ester CH2 CH2 CCH3

O

O CH3 isA) butyl methanoate.B) methyl butanoate.C) methyl butyl ester.D) methyl carboxybutane.

16. The ester obtained by reacting benzyl alcohol and benzoic acid is calledA) benzyl benzeneB) benzyl benzoateC) phenyl benzoateD) benzyl benzate

17. When an ester is saponified, one reaction product isA) a baseB) a carboxylic acidC) an aldehydeD) an alcohol

18. The monomers for the formation of a polyester areA) a dicarboxylic acid and a monoalcohol.B) a dicarboxylic acid and a dialcohol.C) two diesters.D) two monoesters.

19. Which of the following statements concerning acid anhydrides is incorrect?A) They undergo hydrolysis to produce the parent carboxylic acid.B) They are generally less reactive than the corresponding acid chloride.C) They have structures in which three oxygen atoms are present.D) They are produced by reacting two carboxylic acids with each other.

20. Which of the following is the general formula for a phosphate monoester?A)

B)

C)

D)

21. Which of the following is a correct notation for the carboxylic acid functional group.A)

B)C) D) more than one correct responseE) no correct response

22. Which of the following carboxylic acids is paired with its correct IUPAC name?A)

B)

C)

D) more than one correct responseE) no correct response

23. In which of the following pairs of carboxylic acids are both members of the pair dicarboxylic acids?A) malonic acid and succinic acidB) glutaric acid and butyric acidC) oxalic acid and acetic acidD) more than one correct responseE) no correct response

24. For which of the following biochemically important polyfunctional carboxylic acids is its accompanying characterization correct?A) fumaric acid; a keto acidB) pyruvic acid; an unsaturated acidC) lactic acid; a dihydroxy acidD) more than one correct responseE) no correct response

25. Which of the following functional groups is always found at the end of a carbon chain?A) aldehydeB) carboxylic acidC) ketoneD) more than one correct responseE) no correct response

26. Which of the following statements concerning the boiling points of carboxylic acids is correct?A) They are higher than those of corresponding alcohols.B) They are lower than those of corresponding alkanes.C) They are lower than those of corresponding aldehydes.D) more than one correct responseE) no correct response

27. Which of the following compounds could not be oxidized to a carboxylic acid?A) propanalB) 2-methyl-1-propanolC) 2-methyl-2-propanolD) more than one correct responseE) no correct response

28. Which of the following carboxylic acids possesses two acidic hydrogen atoms?A) butanedioic acidB) 2-methylbutanoic acidC) succinic acidD) more than one correct responseE) no correct response

29. In which of the following pairs of compounds does the first listed compound have a greater solubility in water than the second listed compound?A) hexanoic acid, methanoic acidB) sodium butanoate, butanoic acidC) pentanoic acid, potassium pentanoateD) more than one correct responseE) no correct response

30. The general structural difference between a carboxylic acid and an ester is the same as that between anA) alcohol and an ether.B) aldehyde and a ketone.C) alkane and an alkene.D) more than one correct responseE) no correct response

31. Which of the following esters is paired with an incorrect IUPAC name for it?A)

B)

C)

D) more than one correct responseE) no correct response

32. Which of the following pairings of ester common and IUPAC names is correct?A) ethyl propionate and propyl ethanoateB) propyl acetate and propyl ethanoateC) ethyl butyrate and butyl ethanoateD) more than one correct responseE) no correct response

33. Which of the following compounds is a constitutional isomer of ethyl ethanoate?A) methyl methanoateB) ethyl propanoateC) butanoic acidD) more than one correct responseE) no correct response

34. For which of the following types of carboxylic acid derivatives is the parent carboxylic acid(s) a product of the derivative's hydrolysis?A) acid anhydrideB) acid chlorideC) esterD) more than one correct responseE) no correct response

35. Which of the following types of inorganic esters would contain two oxygen-carbon single bonds?A) diphosphate monoesterB) phosphate triesterC) diphosphate diesterD) more than one correct responseE) 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 choicesa) 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) The compound ethanoic acid contains two carbon atoms and two oxygen atoms.(2) Unsubstituted short-chain monocarboxylic acids are completely miscible with water.(3) The two reactants in an esterification reaction are a carboxylic acid and an aldehyde.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) The boiling points of esters are much higher than those of corresponding carboxylic acids.(2) The compound benzoic acid is a heterocylic compound.(3) In linear form, the ester functional group can be represented as -COOR.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) The compound 4-oxobutanoic acid contains both a carboxyl group and a carbonyl group.

(2) Aldehyde oxidation is a method for preparing a carboxylic acid.(3) Both IUPAC and common names for esters consist of two words.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) A carboxylic acid and its corresponding carboxylate ion differ in the number of oxygen atoms they contain.(2) In ester hydrolysis, the carbon-oxygen double bond breaks producing an alcohol and a carboxylic acid.(3) The acronym PET stands for polyester(terephthalate).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.

40. Statements:(1) Hydrogen bonding is not possible between carboxylic acid molecules.(2) The alpha-carbon atom in a carboxylic acid is the carbon atom to which the carboxyl group is attached.(3) Sodium butanoate and ethyl butanoate are both examples of esters.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) Structurally, the difference between malonic acid and succinic acid is a -CH2- grouping.(2) A carboxylic acid salt is generally more soluble in water than the carboxylic acid from which it is obtained.(3) Ester hydrolysis and ester saponification are “reverse” reactions of each other.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) “Pleasant odor” is a general characteristic of esters.(2) Citric acid is both a tricarboxylic acid and a ketoacid.(3) Esters and carboxylic acids with the same number of carbon atoms and the same degree of saturation are constitutional isomers.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) Hydrolysis of a mixed acid anhydride produces two different carboxylic acids as products.(2) Short-chain unsubstituted monocarboxylic acids are strong acids while their longer-chain counterparts are weak acids.(3) The parent alcohol for the ester methyl acetate is methyl 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.

44. Statements:(1) Pyruvic acid is the keto-derivative of propanoic acid.(2) Reaction of a carboxylic acid with a thiol produces a thioester, a compound containing two carbon-sulfur single bonds.(3) One of the products of an esterification reaction is 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.

45. Statements:(1) Nitroglycerin is an example of a phosphate triester.(2) In the body, aspirin is converted to salicylic acid, which is the “active” ingredient.(3) Both ibuprofen and aspirin are propanoic acid derivatives.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.


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 compoundsb) both contain a carbon ring systemc) contain the same number of carbon atoms but are not constitutional isomersd) two names for the same compound

46. Methyl propanoate Propyl methanoate

47. Acetic acid Ethanoic acid

48. Butanedioic acid Butanoic acid

49. Benzoic acid Propyl butanoate

50. 2-Methylpentanoic acid β-Methyl valeric acid


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) twob) threec) fourd) five

51. Saturated four-carbon ester

52. Saturated four-carbon monocarboxylic acid

53. Saturated four-carbon dicarboxylic acid

54. Chlorobenzoic acid

55. Molecular formula of C3H6O2


For each pair of carboxylic acids, select a correct characterization from the response list. Responses may be used more than once or need not be used at all.a) Both are dicarboxylic acids.b) Both are C3 acids.c) Both are monohydroxy acids.d) Both are unsubstituted monocarboxylic acids.

56. Fumaric acid, Succinic acid

57. Citric acid, Lactic acid

58. Glyceric acid, Pyruvic acid

59. Valeric acid, Caproic acid

60. Oxalic acid, Glutaric acid


Identify the missing reactant in each of the reactions using the response list. Responses may be used more than once or need not be used at all.a) waterb) base in waterc) alcohold) carboxylic acid

61. Acid + ? carboxylate ion + H3O+

62. Acid + ? acid salt + H2O

63. Acid + ? ester + H2O

64. Ester + ? acid salt + alcohol

65. Ester + ? acid + alcohol


For each of the inorganic esters, select from the response list the combination of reactants needed to produce the ester. Responses may be used more than once or need not be used at all.

a) one acid molecule one alcohol moleculeb) one acid molecule two alcohol moleculesc) two acid molecules one alcohol moleculed) three acid molecules one alcohol molecule

66.

RO P

O

O

OH

P O P OH

O O

OH OH

67.

RO P

O

OR

OH

68.

HO S

O

OR

O

69.RO N

O

O

70.

O N

O

OCH2

CH

CH2

O N

O

O

O N

O

O

Answer Key

1. B2. C3. C4. D5. B6. D7. C8. C9. A

10. B11. B12. B13. C14. B15. B16. B17. D18. B19. D20. C21. D22. C23. A24. E25. D26. A27. C28. D29. B30. D31. D32. B33. C34. D35. C36. B37. C38. A39. D40. D41. B42. B43. B44. A

45. C46. a47. d48. c49. c50. a51. c52. a53. a54. b55. b56. a57. c58. b59. d60. a61. a62. b63. c64. b65. a66. d67. b68. a69. a70. d

upali/chem121/test/stoker-c16.docx · web viewwhich of the following compounds is a constitutional...

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