Organic Chemistry review Name: 1.

Date:

Which formula represents an unsaturated hydrocarbon? A.

H 2 H C 2 H

C. H

2.

3.

4.

H 2 C H 2 H

B.

H O 2 2 2 C C OH 2 H

D.

6.

H H / . C==C = . / H H H O H 2 2 2 2 H C C C H 2 2 H H

propane

B.

C.

butene

D. benzene

7.

high melting points and are electrolytes

B.

high melting points and are nonelectrolytes

C.

low melting points and are electrolytes

The members of the alkene series of hydrocarbons are similar in that each member has the same A.

empirical formula

B.

general formula

C.

structural formula

D. molecular formula

pentene 8.

Petroleum, a starting material for many chemical products, is a complex natural mixture of A.

aldehydes

B.

C.

hydrocarbons

D. ketones

What is the number of hydrogen atoms in a molecule of ethyne? A.

9.

ethers

6

B.

2

C.

8

low melting points

Which formula represents a hydrocarbon with a double covalent bond?

B.

low vapor pressure

C.

high conductivity in solution

A.

CH3 Cl

B.

D. high boiling points

C.

C2 H2

D. C2 H4

C2 H3 Cl

The total number of covalent bonds in a molecule of methane is A.

1

B.

2

C.

3

D. 4 11.

Which compound is a member of the alkene series of hydrocarbons? A.

benzene

B.

C.

toluene

D. butadiene

propene

Which compound contains a triple bond? A.

page 1

D. 4

Organic compounds that are essentially non-polar and exhibit weak intermolecular forces have A.

10. 5.

A.

D. low melting points and are nonelectrolytes

The hydrocarbon C7 H8 belongs to the same homologous series of hydrocarbons as A.

Organic compounds di er from inorganic compounds in that organic compounds generally have

CH4

B.

C 2 H2

C.

C3 H6

D. C4 H10

12.

Which formula represents a saturated hydrocarbon? A.

13.

14.

15.

CH4

B.

C 2 H4

C.

C3 H6

D. C4 H8

A.

ethene

B.

C.

ethylene

D. ethyne

decreases

B.

C.

remains the same

ethane 18.

H

A.

increases

19.

B.

H 2 C 2 H H

H 2 C H 5 2 H

10

D. H

H 2 C 2 H

H 2 C 2 2 2 C 2 H

H 2 C 2 H

R

C. H

R1 20.

H

C==C = 2 2 H H

A.

butane

B.

C.

ethane

D. methane

O 2 2 C R2

R1

B.

8

C.

6

D. 4

O . C / H

B. R

O 2 2 C R2

D. R1

O . C / OH O

R2

Which is the structural formula for propanone (acetone)? A. H

H 2 C 2 H

H 2 C 2 OH

H 2 C 2 H

H

H 2 C 2 H

H 2 C 2 H

H 2 C==O =

H C.

Which hydrocarbon is the most abundant component of natural gas?

H

OH

The general formula for aldehyde is A.

H

C.

D.

R

O 2 2 C O

R

What is the total number of hydrogen atoms in a molecule of butene?

Which compound belongs to the hydrocarbon series with the general formula Cn H2n ? H C==C =

B.

R

O 2 2 C H

C.

As the length of the chain of carbon atoms in molecules of the alkene series increases, the number of double bonds per molecule A.

Which is the general formula for an aldehyde? A.

Which compound is a saturated hydrocarbon?

A.

16.

17.

B. H

H

H 2 C C 2 2 2 H O

H 2 C 2 H

H

H 2 C 2 OH

H 2 C H 2 OH

D.

H 2 C 2 OH

H

propane

page 2

Organic Chemistry review

21. H H

H 2 C 2 C 2 H

22. H

H H

C 2 C 2 C 2 H

Which functional group is found in all organic acids? A.

H

H 2 C 2 H

H H

C.

1-methyl-2-ethylethane

B.

1-propylethane

C.

n-propane

23.

H 2 C 2 H

H

H 2 C==O =

Which is the correct IUPAC name for the hydrocarbon with the structural formula shown? A.

B.

D.

O . C / OH

Which general formula represents a ketone? A.

O 2 2 C R2

R1

D. n-pentane C.

R

OH

B. R1 D. R

24.

25.

Behavior Tested High Melting Point Low Melting Point Soluble in Water

Insoluble in Water

Decomposed Under High Heat Stable Under High Heat Electrolyte

Nonelectrolyte

Sample I X

Sample II X

X

X X

X X

X

Sample III X

OH

O 2 2 C O

R2

O . C / OH

All organic compounds must contain the element A.

hydrogen

B.

nitrogen

C.

carbon

D. oxygen

Sample IV

X X X

X X

X X

A student investigated samples of four di erent substances in the solid state. The table is a record on the behaviors observed (marked with an X) when each solid was tested. Based on the tabulated results, which of the solids investigated has the characteristics most closely associated with those of an organic compound? A.

Sample I

B.

Sample II

C.

page 3

Sample III

D. Sample IV

Organic Chemistry review

26.

27.

Which hydrocarbon contains a triple bond? A.

butane

B.

C.

ethene

D. ethyne

CH3

32. HO

benzene

C CH3 2 2 O

A.

A.

ethers

B.

C.

alcohols

D. aldehydes

29.

33.

ketones

C3 H8

B.

C 4 H8

C.

C5 H8

D. C7 H8

Alkanes di er from alkenes in that alkanes A.

are hydrocarbons

B.

have the general formula Cn H2n

C.

are saturated compounds

34.

R

H 2 C 2 H

31.

CH

CH2

C.

3

D. 4

B.

C.

an aldehyde

D. an acid

35.

D. CH4

an ether

Which is the general formula for organic acids?

C.

CH3

C.

an ester

OH

B.

2

A.

R

In the molecule represented by the formula shown, R could be A.

B.

O . CH3 CH2 C / H

A.

D. undergo addition reactions 30.

1

Which type of compound is represented by the structural formula shown?

Which compound is a member of the hydrocarbon series with the general formula Cn H2n 6 ? A.

O . C / OH

How many di erent functional groups are there in a molecule with the structural formula shown?

The molecule shown is a member of a class of organic compounds called

28.

H 2 C 2 H

O . C / H

R1 / C==O = . R2

B. R

D. R1

O . C / OH O

R2

A common gaseous fuel that is often found with petroleum is A.

carbon monoxide

B.

carbon dioxide

C.

methane

D. ethene

Which formula represents an organic acid? A.

CH3 COOH

B.

CH3 CHO

C.

CH3 COCH3

D. CH3 OH

page 4

Organic Chemistry review

36. H

H 2 C 2 H

H 2 C 2 H

O

H 2 C 2 H

H 2 C 2 H

37. H

If a hydrocarbon molecule contains a triple bond, its IUPAC name ends with A.

Which type of compound is represented by the structural formula shown? A.

a ketone

B.

C.

an ester

D. an ether

38.

an aldehyde

Characteristic Tested

Substance A B C D

High Melting Point

X

Low Melting Point

Stable under High Heat

1

B.

2

C.

3

D. 4

CH4

B.

C 2 H4

C.

C3 H6

D. C4 H8

X

X X

Electrolyte

D. “yne”

X X

Decomposed under High Heat

“one”

X

X

Insoluble in Water

C.

X X

Soluble in Water

“ene”

Which hydrocarbon formula is also an empirical formula? A.

40.

B.

What is the maximum number of covalent bonds that an atom of carbon can form? A.

39.

“ane”

X

X

Nonelectrolyte

X X

X

X

A student investigated four di erent substances in the solid phase. The table shown is a record of the characteristics (marked with an X) exhibited by each substance. Which substance has characteristics most like those of an organic compound? A. 41.

B.

A

C.

B

Given the structural formula for ethyne: H

C

C

42.

H

What is the name of the compound with the following formula?

What is the total number of electrons shared between the carbon atoms? A.

6

B.

2

C.

3

D. D

C

H

D. 4

page 5

H O H 2 2 2 2 C C C 2 2 H H

H

A.

propanone

B.

propanol

C.

propanal

D. propanoic acid

Organic Chemistry review

43.

What is the general formula for an ether? A.

R1 O R2

B.

C.

O 2 2 C

D.

R

H

48.

R OH

R

O 2 2 C

Ethene (common name ethylene) is a commercially important organic compound. Millions of tons of ethene are produced by the chemical industry each year. Ethene is used in the manufacture of synthetic bers for carpeting and clothing, and it is widely used in making polyethylene. Low-density polyethylene can be stretched into a clear, thin lm that is used for wrapping food products and consumer goods. High-density polyethylene is molded into bottles for milk and other liquids. Ethene can also be oxidized to produce ethylene glycol, which is used in antifreeze for automobiles. The structural formula for ethylene glycol is:

OH

44. Which structural formula represents a saturated hydrocarbon?

45.

46.

A.

B.

C.

D.

Which structural formula represents a saturated hydrocarbon? A.

B.

C.

D.

Base your answer(s) to the following question(s) on the information below.

At standard atmospheric pressure, the boiling point of ethylene glycol is 198 C, compared to ethene that boils at 104 C. Explain, in terms of bonding, why ethene is an unsaturated hydrocarbon. 49.

Given the equation: C2 H6 + Cl2 ! C2 H5 Cl + HCl described as

Which formula represents a hydrocarbon? A.

CH3 CH2 CH2 CHO

B.

CH3 CH2 CH2 CH3

C.

CH3 CH2 CH2 COOH

D. CH3 CH2 COOCH3

A.

addition involving a saturated hydrocarbon

B.

addition involving an unsaturated hydrocarbon

C.

substitution involving a saturated hydrocarbon

D. substitution involving an unsaturated hydrocarbon 47.

Which element must be present in an organic compound? A.

hydrogen

B.

oxygen

C.

carbon

D. nitrogen page 6

Organic Chemistry review

50.

Base your answer(s) to the following question(s) on the information below.

53. H

The hydrocarbon 2-methylpropane reacts with iodine as represented by the balanced equation below. At standard pressure, the boiling point of 2-methylpropane is lower than the boiling point of 2-iodo-2-methylpropane.

H 2 C 2 H

A.

Explain, in terms of bonding, why the hydrocarbon 2-methylpropane is saturated. Base your answer(s) to the following question(s) on the information below.

H

H 2 C 2 H

O . C / H

H

H 2 C 2 H

H 2 C 2 H

C. H

Gasoline is a mixture composed primarily of hydrocarbons such as isooctane, which is also known as 2,2,4-trimethylpentane. Gasoline is assigned a number called an octane rating. Gasoline with an octane rating of 87 performs the same as a mixture that consists of 87% isooctane and 13% heptane. An alternative fuel, E-85, can be used in some automobiles. This fuel is a mixture of 85% ethanol and 15% gasoline.

D. H

In the space provided, draw a structural formula for a molecule of 2,2,4-trimethylpentane. 52.

H

Which is an isomer of the compound shown?

B.

51.

O . C / O

O . C / O

H 2 C 2 O 2 H

H 2 C 2 O 2 H

O . C / O

H 2 C 2 H

H

H

H

Base your answer(s) to the following question(s) on the information below. In one industrial organic reaction, C3 H6 reacts with water in the presence of a catalyst. This reaction is represented by the balanced equation below.

Write the IUPAC name for the organic reactant.

page 7

Organic Chemistry review

54. H

H 2 C 2 H

H 2 C 2 H

57.

O . C / H

Which structural formula represents an isomer of dimethyl ether? A. H

Which compound is an isomer of the one shown? A. H

H 2 C C 2 2 2 H O

H 2 C 2 H

H

H 2 C 2 H

H 2 C 2 H

O . C / OH

H

H 2 C 2 H

H 2 C 2 H

H 2 C 2 H

H

H 2 C 2 H

C

O . H

B.

C.

D.

55.

56.

C.

H

H

58.

OH

A.

butane

B.

ethane

C.

pentane

D. propane

O . C / H

B.

O . C OH

H

H 2 C 2 H

OH

H

H 2 C 2 H

H 2 C 2 H

D.

A.

decreases

B.

C.

remains the same

H

H 2 C 2 H

H 2 C 2 H

H 2 C 2 H

H 2 C 2 H

OH

H

H 2 C 2 H

H 2 C 2 H

H 2 C 2 OH

H 2 C 2 H

H

increases

Which is an accurate description of the two compounds shown?

Which is the structural formula for an unsaturated compound?

A.

They are isotopes of butanol.

B.

They are isomers of butanol.

A.

C.

They are alkanes.

H

H 2 C 2 H

H 2 C 2 H

H

H 2 C 2 H

H 2 C 2 H

C.

B.

H

Cl

D. OH

H

C==C = H 2 2 Cl Cl

H 2 C 2 H

OH

As the number of carbon atoms in a hydrocarbon molecule increases, the number of possible isomers generally

59.

Which of the following compounds has the greatest possible number of isomers?

H 2 C 2 H

O

H 2 C 2 H

D. They are alkenes.

H

page 8

Organic Chemistry review

60. H

H 2 C 2 H

63. H

H 2 C 2 H

H 2 C 2 H

OH

Which is an isomer of the compound shown?

A.

A.

H

H 2 C 2 H

H 2 C 2 H

O

H

H O 2 2 2 C C 2 H

H 2 C 2 H

H

H 2 C 2 H

H 2 C 2 H

H 2 C 2 H

H

H 2 C 2 H

H 2 C 2 H

O . C / OH

C.

D.

62.

H 2 C==O =

Which structural formula represents an isomer?

B.

61.

H 2 C 2 H

H 2 C 2 H

H

B. H

HO

C. OH

A.

molecular formula

B.

C.

number of atoms

D. formula mass

CH3 Br and CH2 Br2

B.

CH3 OH and CH3 CH2 OH

C.

CH3 OH and CH3 CHO

H 2 C 2 H

H

H

H

H 2 C 2 H

H 2 C 2 H

H

O

H 2 C 2 H

H

64. Which compounds are isomers?

molecular structure

Which compounds are isomers? A.

H 2 C 2 H

O

H 2 C 2 H

H O 2 2 2 C C H 2 H

D.

The isomers CH3 OCH3 and CH3 CH2 OH di er in

H 2 C 2 H

A.

CH3 OH and CH3 CH2 OH

B.

CH4 and CCl4

C.

CH3 CH2 CHO and CH3 COCH3

D. CH3 CH2 OH and CH3 CH2 COOH

D. CH3 OCH3 and CH3 CH2 OH

page 9

Organic Chemistry review

65.

Which formula is an isomer of butane?

67.

A.

68.

B.

The reaction CH4 + Br2 ! CH3 Br + HBr is an example of A.

addition

B.

hydrogenation

C.

substitution

D. polymerization

Which molecule is represented by X in this reaction? H C C H + 2Br2 ! X A. H

H 2 C 2 H

H 2 C 2 H

H

H 2 C 2 H

H 2 C Br 2 Br

C. C.

69.

D.

70. 66.

H

H 2 C 2 H

H 2 C 2 H

Cl

H 2 C 2 H

H 2 C 2 H

C.

B. Cl

H

H 2 C 2 H

Cl

Cl

H 2 C 2 H

Cl

D. Cl

Br

H

H 2 C 2 Br

H 2 C H 2 Br

H

Br 2 C 2 Br

Br 2 C H 2 Br

D.

The reaction nC2 H4 ! ( C2 H4 )n is an example of A.

substitution

B.

C.

saponi cation

D. esteri cation

polymerization

In the reaction shown, what is the formula of the product represented by the X ? H H / . C==C = + Br2 ! X . / H H

Which is the product of the reaction between ethene and chlorine? A.

B.

A. H

H 2 C 2 H

H 2 C 2 H

H

H

H 2 C H 2 Br

D. H

H

H 2 C 2 Br

C.

page 10

B.

H 2 C 2 H

Br 2 C H 2 H

C==C = H 2 2 Br Br

Organic Chemistry review

71.

72.

The process of joining many monomers is called A.

saponi cation

B.

C.

polymerization

D. substitution

77.

fermentation

Which are the products of a fermentation reaction? A.

an ester and water

B.

a salt and water

C.

an alcohol and carbon dioxide

74.

75.

76.

A.

oxidation of alcohols to form a ketone

B.

oxidation of alcohols to form an acid

C.

dehydration of alcohols to form a polymer

D. dehydration of alcohols to form an ether 78.

D. a soap and glycerol 73.

The equation CH3 OH + CH3 OH ! CH3 OCH3 + H2 O illustrates the

In the equation CH3 OH + oxidizing agent ! X + H2 O, the product represented by X is A.

an alcohol

B.

C.

an ether

D. a ketone

79.

an aldehyde

One of the products of condensation polymerization is A.

water

B.

C.

a monomer

D. a ketone

80.

Which type of reaction is used in the production of nylon? A.

substitution

B.

C.

esteri cation

D. polymerization

The products of condensation polymerization are polymer and A.

carbon dioxide

B.

C.

ethanol

D. glycerol

C6 H12 O6 ! 2C2 H5 OH + 2CO2 The chemical process illustrated by this equation is

Which hydrocarbon will undergo a substitution reaction with chlorine methane

B.

C.

propene

D. butene

water

Given the equation:

an acid

A.

saponi cation

A.

fermentation

B.

saponi cation

C.

esteri cation

D. polymerization

ethyne

Esteri cation is the reaction of an acid with A.

water

B.

an alcohol

C.

a base

D. a salt

page 11

Organic Chemistry review

Problem-Attic format version 4.4.178 c 2011–2013 EducAide Software _ Licensed for use by Simone Shaker Terms of Use at www.problem-attic.com Organic Chemistry review

05/21/2013

1. Answer:

B

20. Answer:

B

2. Answer:

D

21. Answer:

D

3. Answer:

C

22. Answer:

D

4. Answer:

D

23. Answer:

A

5. Answer:

D

24. Answer:

C

6. Answer:

D

25. Answer:

B

7. Answer:

B

26. Answer:

D

8. Answer:

B

27. Answer:

B

9. Answer:

A

28. Answer:

D

10. Answer:

B

29. Answer:

B

11. Answer:

B

30. Answer:

C

12. Answer:

A

31. Answer:

A

13. Answer:

B

32. Answer:

B

14. Answer:

C

33. Answer:

C

15. Answer:

D

34. Answer:

B

16. Answer:

D

35. Answer:

C

17. Answer:

A

36. Answer:

D

18. Answer:

B

37. Answer:

D

19. Answer:

A

38. Answer:

D

Teacher's Key 39. Answer:

A

53. Answer:

C

40. Answer:

B

54. Answer:

A

41. Answer:

A

55. Answer:

C

42. Answer:

A

56. Answer:

B

43. Answer:

A

57. Answer:

D

44. Answer:

C

58. Answer:

B

45. Answer:

A

59. Answer:

B

46. Answer:

C

60. Answer:

B

47. Answer:

C

61. Answer:

B

48. Answer:

Has a carbon-carbon double bond.

62. Answer:

D

49. Answer:

B

63. Answer:

A

64. Answer:

C

65. Answer:

D

66. Answer:

C

67. Answer:

C

68. Answer:

D

69. Answer:

B

70. Answer:

C

71. Answer:

C

72. Answer:

C

73. Answer:

B

74. Answer:

A

50. Answer:

A 2-methylpropane molecule has only single carbon-carbon bonds. There are only single bonds in methylpropane.

no multiple bonds between carbon atoms 51. Answer:

52. Answer:

or

propene

Page 2

Teacher's Key 75. Answer:

A

76. Answer:

B

77. Answer:

D

78. Answer:

D

79. Answer:

B

80. Answer:

A

Page 3