REGENTS CHEMISTRY Organic Chemistry Practice Test Name ______________________

Mr. Dolgos Period ____

1. Which organic compound is a saturated 9. Natural gas is mostly comprised of

hydrocarbon? A) methane B) butane
A) ethane B) ethanol C) propane D) ethane
C) ethyne D) ethene
10. Molecules of 2-methyl-propane and n-butane differ
2. Which compound is a saturated hydrocarbon? in their
A) hexane B) hexanal A) number of covalent bonds
C) hexanol D) hexene B) molecular formulas
C) structural formulas
3. Which structural formula correctly represents a D) number of carbon atoms
hydrocarbon molecule?
A) B) 11. Which formula represents butane?
A) CH3CH2CH3 B) CH3CH2CH2CH3
C) CH3CH3 D) CH3CH2CH2CH2CH3

12. Which of the following compounds has the greatest

C) D)
possible number of isomers?
A) propane B) butane
C) ethane D) pentane

13. What is the total number of carbon atoms

4. In saturated hydrocarbons, carbon atoms are
contained in an ethyl group?
bonded to each other by
A) 1 B) 2
A) alternating double and triple covalent bonds
B) alternating single and double covalent bonds C) 3 D) 4

C) single covalent bonds, only

14. Each member in the alkane series of hydrocarbons,
D) double covalent bonds, only
when considered in successive order, has 1 more
carbon atom and how many more hydrogen atoms?
5. Which compound is classified as a hydrocarbon?
A) 1 B) 2
A) chloroethane B) ethanoic acid
C) 3 D) 4
C) ethanol D) ethane

15. Which formula represents an unsaturated

6. Which formula represents a molecule of a
hydrocarbon?
saturated hydrocarbon?
A) CH2CHCl B) CH3CHCH2
A) C2H2 B) C4H10
C) CH3CH2CH3 D) CH3CH2Cl
C) C6H6 D) C5H8

16. Given the structural formula:

7. What is the general formula for the members of
the alkane series?
A) CnH2n B) CnH2n+2
C) CnH2n–2 D) CnH2n–6

8. In which group could the hydrocarbons all belong to

the same alkene series?
A) C2H4, C3H6, C4H8 B) C2H2, C2H4, C2H6
What is the IUPAC name of this compound?
C) C2H4, C2H6, C3H6 D) C2H2, C2H4, C4H8
A) propene B) propane
C) propanone D) propanal

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17. Which structural formula represents a molecule of 20. Which structural formula represents a member of
butane? the alkene series?
A) A)

B)
B)

C)

C)

D)

D)

21. Which compound is a member of the same

homologous series as C3H6?
A) C3H8 B) C2H6
18. The empirical formula of a compound is CH2. Which
C) C2H4 D) C3H4
molecular formula is correctly paired with a
structural formula for this compound?
22. Given the structural formula for ethyne:
A)

B)
What is the total number of electrons shared
between the carbon atoms?
A) 6 B) 2
C) 3 D) 4
C)
23. The compounds 2-butanol and 2-butene both contain
A) carbon atoms B) oxygen atoms
C) double bonds, only D) single bonds, only

D) 24. Which element has atoms that can bond with each
other to form long chains or rings?
A) oxygen B) fluorine
C) nitrogen D) carbon

19. In which pair of hydrocarbons does each compound

25. Which element must be present in an organic
contain only one double bond per molecule?
compound?
A) C4H8 and C2H4 B) C2H2 and C3H6
A) carbon B) nitrogen
C) C6H6 and C7H8 D) C2H2 and C2H6
C) oxygen D) hydrogen

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26. Which structural formula represents 2-pentyne? 29. Compared with the rate of an inorganic reaction,
A) the rate of an organic reaction is usually
A) slower, because organic compounds are ionic.
B) faster, because the organic compounds are
molecules.
C) faster, because organic compounds are ionic.
D) slower, because the organic compounds are
molecules.
B)
30. Organic compounds differ from inorganic
compounds in that organic compounds generally have
A) high melting points and are nonelectrolytes
B) high melting points and are electrolytes
C) C) low melting points and are electrolytes
D) low melting points and are nonelectrolytes

31. Which of the following has the lowest boiling point?

A) ethane B) methane
D)
C) butane D) propane

32. In a given homologous series of hydrocarbons, the

boiling point generally increases as the size of the
molecules increases. The best explanation for this
statement is that in larger organic molecules
A) the molecules are more symmetrical
B) there are greater intermolecular forces
C) the number of covalent bonds per molecule is
27. Organic compounds that are essentially non-polar greater
and exhibit weak intermolecular forces have D) more hydrogen bonding is possible
A) low melting points
33. Which formula is an isomer of butane?
B) low vapor pressure
C) high boiling points A) B)
D) high electrical conductivity in solution

28. Which representation is the structural formula of

an organic compound?
A) B)

C) D)

C) D)

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34. Given the compound: 39. Which organic compound is a weak electrolyte?
A) pentane B) ethanoic acid
C) carbon tetrachloride D) benzene

40. In an aqueous solution, which substance yields

hydrogen ions as the only positive ions?
A) CH3COOH B) KOH
Which structural formula represents an isomer? C) C2H4 D) CH4
A) B)
41. Which compound is an alcohol?
A) methanol B) butane
C) ethyne D) propanal

C) D)
42. A compound with the formula CH3CH2OH is
classified as an
A) acid B) alkane
C) alcohol D) alkene

35. The four single bonds of a carbon atom are 43. Which structural formula represents a
spatially directed toward the corners of a regular monohydroxy alcohol?
A) rectangle B) tetrahedron A)
C) triangle D) square

36. Which of these compounds has chemical properties

most similar to the chemical properties of ethanoic
acid? B)
A) C2H5COOC2H5 B) C3H7COOH
C) C2H5OH D) C2H5OC2H5

37. Which organic compound will dissolve in water to

produce a solution that will turn blue litmus red? C)

A) B)

D)

C) D)

44. Methanal is the IUPAC name for an

A) ether B) alcohol
38. Which statement is true for a compound whose
C) aldehyde D) acid
formula is CH3CH2COOH?
A) It is an acid. 45. Which formula represents a ketone?
B) Its solution turns litmus blue.
A) HCHO B) CH3COCH3
C) It is an alcohol.
C) HCOOH D) CH3CH2OH
D) Its solution turns phenolphthalein pink.

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46. Which structural formula represents a primary 48. The general formula for aldehydes is
alcohol? A) B)
A)

C) D)
B)

C) 49. What is the name of the compound with the

following formula?

D)

A) propanone B) propanal
C) propanol D) propanoic acid

47. Which structural formula represents a secondary 50. What is the minimum number of carbon atoms a
alcohol? ketone may contain?
A) A) 1 B) 2
C) 3 D) 4

51. What is the correct formula of 1,1-dibromoethane?

A) B)
B)

C) D)

C)

52. Which is an isomer of 2-chloropropane?

D)
A) 1-chlorobutane B) 1-chloropropane
C) butane D) propane

53. The compound CH3COOCH3 is classified as

A) an acid B) a hydrocarbon
C) an alcohol D) an ester

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54. Given the formula: 58. Which formula represents an ether?
A)

B)

This compound is classified as

A) an amide B) a ketone
C)
C) an amine D) an aldehyde

55. Given the structural formula:

D)

59. As an addition reaction occurs, the number of

electrons shared between carbon atoms
A) decreases B) increases
This structural formula represents a molecule of
C) remains the same
A) a ketone B) an aldehyde
C) an amino acid D) an ester 60. Given the organic reaction:

56. Given the structural formula:

This reaction is an example of

A) addition B) saponification
The compound represented by this formula can be C) substitution D) fermentation
classified as an
A) ester B) organic acid 61. Which is an example of an addition reaction?
C) ether D) aldehyde A) CH3COOH + CH3OH → CH3COOCH3 + H2O

57. Which structural formula represents an ether? B) C2H6 + Cl2 → C2H5Cl + HCl
C) C3H6 + H2 → C3H8
A) B)
D) C6H12O6 → 2 C2H5OH + 2 CO2

62. In which type of reaction can an unsaturated

hydrocarbon become saturated?
A) reduction with oxygen
C) D) B) addition
C) substitution with hydrogen
D) oxidation with oxygen

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63. Given the equation: 71. Given the equation:

CH4 + Br2 → CH3Br + HBr

Which type of reaction does this equation

represent?
A) substitution B) hydrogenation
C) addition D) polymerization

64. As a substitution reaction occurs, the number of

electrons shared between carbon atoms
A) decreases B) increases Which type of reaction is represented?
C) remains the same A) esterification
B) addition polymerization
65. Which organic product is formed by the reaction
C) condensation polymerization
below?
D) saponification

72. Which alcohol reacts with C2H5COOH to produce

the ester C2H5COOC2H5?
A) C4H9OH B) C2H5OH
C) C3H7OH D) CH3OH

73. Which compound will react with CH3COOH to form

A) bromobenzene B) bromoethene
the ester methyl ethanoate?
C) bromoethane D) bromoethyne
A) CH3COOH B) CH3OCH3

66. The process of joining many small molecules into C) CH3COCH3 D) CH3OH
larger molecules is called
74. A reaction between an acid and alcohol produces an
A) substitution B) neutralization
ester and
C) saponification D) polymerization
A) glycerol B) ethanol

67. Which organic reaction produces rubber and C) carbon dioxide D) water
plastics?
75. What are the two main products of a fermentation
A) esterification B) polymerization
reaction?
C) saponification D) fermentation
A) sugar and water
B) sugar and carbon dioxide
68. Cellulose, protein, and starch are classified as
C) ethanol and water
A) synthetic polymers B) esters
D) ethanol and carbon dioxide
C) natural polymers D) aldehydes
76. What are the products of a fermentation reaction?
69. A condensation polymerization reaction produces a
A) an alcohol and carbon monoxide
polymer and
B) a salt and an acid
A) H2O B) O2
C) an alcohol and carbon dioxide
C) CO2 D) H2
D) a salt and water

70. The fermentation of C6H12O6 will produce CO2 and

77. The hydrolysis of a fat by a base is called
A) C2H5OH B) Ca(OH)2
A) polymerization B) neutralization
C) C3H5(OH)3 D) Cr(OH)3
C) esterification D) saponification

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78. Which reaction best represents the complete
combustion of ethene?
A) C2H4 + HCl → C2H5Cl
B) C2H4 + Cl2 → C2H4Cl2
C) C2H4 + 3 O2 → 2 CO2 + 2 H2O
D) C2H4 + H2O → C2H5OH

79. Which products are obtained when CH4(g) burns

completely in an excess of oxygen?
A) CO2 and CO B) CO and C
C) CO2 and H2O D) CO and H2O

80. The principal products of saponification, a reaction

between a fat and a base, are soap and
A) carbon dioxide B) water
C) ethyl alcohol D) glycerol

Base your answers to questions 81 and 82 on the

information below.

Given the reaction between 1-butene and chlorine gas:

C4H8 + Cl2 → C4H8Cl2

81. Which type of chemical reaction is represented by

this equation?

82. Draw the structural formula of the product 1,2-

dichlorobutane.

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Base your answers to questions 83 through 86 on the information and diagram below and on your knowledge of chemistry.

Crude oil is a mixture of many hydrocarbons that have different numbers of carbon atoms. The use of a fractionating
tower allows the separation of this mixture based on the boiling points of the hydrocarbons.
To begin the separation process, the crude oil is heated to about 400°C in a furnace, causing many of the hydrocarbons of
the crude oil to vaporize. The vaporized mixture is pumped into a fractionating tower that is usually more than 30 meters
tall. The temperature of the tower is highest at the bottom. As vaporized samples of hydrocarbons travel up the tower, they
cool and condense. The liquid hydrocarbons are collected on trays and removed from the tower. The diagram below illustrates
the fractional distillation of the crude oil and the temperature ranges in which the different hydrocarbons condense.

83. State the trend between the boiling point of the hydrocarbons contained in the crude oil and the number of carbon
atoms in these molecules.

84. Describe the relationship between the strength of the intermolecular forces and the number of carbon atoms in the
different hydrocarbon molecules.

85. Write an IUPAC name of one saturated hydrocarbon that leaves the fractionating tower at less than 40°C.

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86. How many hydrogen atoms are present in one molecule of octane?

87. Base your answers to the following questions on the information below.

Gasoline is a mixture of hydrocarbons, one of which is octane. Sometimes water gets into the fuel
tank of the automobile. Because it can not mix with the gasoline, it sinks to the bottom of the fuel
tank. In cold weather the water can sometimes freeze in the gas lines and interrupt the flow of
gasoline to the engine. An additive that contains the alcohol, methanol, can be added to the fuel tank
that prevents the freezing of water by forming a solution with water that won't freeze.

a Draw the structural formula of the gasoline component, octane.

b Draw the structural formula of the gasoline additive, methanol.

c Explain why the water can dissolve in the alcohol, methanol, but not dissolve in the gasoline.

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Answer Key

1. A 26. B

2. A 27. A

3. C 28. C

4. C 29. D

5. D 30. D

6. B 31. B

7. B 32. B

8. A 33. B

9. A 34. D

10. C 35. B

11. B 36. B

12. D 37. C

13. B 38. A

14. B 39. B

15. B 40. A

16. A 41. A

17. D 42. C

18. A 43. D

19. A 44. C

20. B 45. B

21. C 46. A

22. A 47. D

23. A 48. D

24. D 49. A

25. A 50. C

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Answer Key

51. D 76. C

52. B 77. D

53. D 78. C

54. A 79. C

55. C 80. D

56. C 81. addition; chlorination; halogenation; redox; synthesis

57. A 82. Essay

58. A 83. As the number of carbon atoms in these molecules

increases, the boiling point increases.
59. A
84. The intermolecular forces are weaker for molecules that
60. A have fewer carbon atoms.

61. C 85. methane; ethane; propane; methyl propane; butane

62. B 86. 18

63. A 87. a) Drawing; b) Drawing; c) Water and alcohol are both

similar (polar) and "like dissolves like."
64. C

65. C

66. D

67. B

68. C

69. A

70. A

71. C

72. B

73. D

74. D

75. D

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Name ________________________________ Class __________________________ Date ___________

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