Organic Chemistry review

Name: Date:

1. Which formula represents an unsaturated 6. Organic compounds di er from inorganic

hydrocarbon? compounds in that organic compounds generally
have
A. H H B. H H
2 2 / . A. high melting points and are electrolytes
H C C H C==C
=
2 2 . / B. high melting points and are nonelectrolytes
H H H H
C. low melting points and are electrolytes
C. H O D. H O H
2 2
2 2 2
2 2 D. low melting points and are nonelectrolytes
H C C OH H C C C H
2 2 2
7. The members of the alkene series of hydrocarbons
H H H are similar in that each member has the same

2. The hydrocarbon C7 H8 belongs to the same A. empirical formula B. general formula

homologous series of hydrocarbons as
C. structural formula D. molecular formula
A. propane B. pentene

C. butene D. benzene 8. What is the number of hydrogen atoms in a

molecule of ethyne?

3. Petroleum, a starting material for many chemical A. 6 B. 2 C. 8 D. 4

products, is a complex natural mixture of

A. aldehydes B. ethers 9. Organic compounds that are essentially non-polar

and exhibit weak intermolecular forces have
C. hydrocarbons D. ketones
A. low melting points
4. Which formula represents a hydrocarbon with a B. low vapor pressure
double covalent bond?
C. high conductivity in solution
A. CH3 Cl B. C2 H3 Cl D. high boiling points
C. C2 H2 D. C2 H4
10. Which compound is a member of the alkene series
of hydrocarbons?
5. The total number of covalent bonds in a molecule
of methane is
A. benzene B. propene
A. 1 B. 2 C. 3 D. 4 C. toluene D. butadiene

11. Which compound contains a triple bond?

A. CH4 B. C 2 H2 C. C3 H6 D. C4 H10

page 1
12. Which formula represents a saturated hydrocarbon? 17. Which is the general formula for an aldehyde?

A. CH4 B. C 2 H4 C. C3 H6 D. C4 H8 A. O B. R OH
2
2
R C H
13. Which compound is a saturated hydrocarbon?
C. O D. O
2
2 2
2
A. ethene B. ethane R C O H R1 C R2
C. ethylene D. ethyne
18. What is the total number of hydrogen atoms in a
molecule of butene?
14. As the length of the chain of carbon atoms in
molecules of the alkene series increases, the
number of double bonds per molecule A. 10 B. 8 C. 6 D. 4

A. decreases B. increases 19. The general formula for aldehyde is

C. remains the same
A. O B. O
. .
15. Which compound belongs to the hydrocarbon R C R C
series with the general formula Cn H2n ? / /
H OH
A. H C==C
= H B. H H H C. O D. R1 O R2
2 2 2 2
2
H C C C H R1 C R2
2 2 2
H 2 H
2 20. Which is the structural formula for propanone
(acetone)?
H C H
2
H A. H H H B. H H
2 2 2 2 2
C. H D. H
H C C C H H C C C H
2 2
2 2 2 2 2
2 2
C H H C C==C
= H
5 2 H OH H H O H
2 2 2
H H H H C. H H H D. H H H
2 2 2 2 2 2
H C C C==O
= H C C C H
16. Which hydrocarbon is the most abundant
component of natural gas? 2 2 2 2 2
H H OH OH OH

A. butane B. propane

C. ethane D. methane

page 2 Organic Chemistry review

21. H 22. Which functional group is found in all organic
2 acids?
H C H
2 A. H B. H
H C C H 2 2
2 2 C H C OH
H H C H 2 2
2 H H
H C H
2 C. H D. O
H 2 .
C==O
= C
Which is the correct IUPAC name for the
/
hydrocarbon with the structural formula shown?
OH

A. 1-methyl-2-ethylethane
23. Which general formula represents a ketone?
B. 1-propylethane
A. O B. O
C. n-propane
2
2 2
2
D. n-pentane R1 C R2 R1 C O R2

C. R OH D. O
.
R C
/
OH

24. All organic compounds must contain the element

A. hydrogen B. nitrogen

C. carbon D. oxygen

25. Sample Sample Sample Sample

Behavior Tested I II III IV
High Melting Point X X
Low Melting Point X X
Soluble in Water X X
Insoluble in Water X X
Decomposed Under High Heat X
Stable Under High Heat X X X
Electrolyte X X
Nonelectrolyte 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. Sample III D. Sample IV

page 3 Organic Chemistry review

26. Which hydrocarbon contains a triple bond? 32. H O
2 .
HO C C
A. butane B. benzene
2 /
C. ethene D. ethyne H OH
How many di erent functional groups are there in
a molecule with the structural formula shown?
27. CH3 C CH3
2
2
O A. 1 B. 2 C. 3 D. 4

The molecule shown is a member of a class of

organic compounds called 33. O
.
A. ethers B. ketones CH3 CH2 C
/
C. alcohols D. aldehydes H
Which type of compound is represented by the
28. Which compound is a member of the hydrocarbon structural formula shown?
series with the general formula Cn H2n 6 ?
A. an ester B. an ether
A. C3 H8 B. C 4 H8 C. C5 H8 D. C7 H8
C. an aldehyde D. an acid

29. Alkanes di er from alkenes in that alkanes

34. Which is the general formula for organic acids?

A. are hydrocarbons
A. O B. O
B. have the general formula Cn H2n . .
R C R C
C. are saturated compounds / /
H OH
D. undergo addition reactions
C. R1 D. R1 O R2
/
30. H C==O
=
2 .
R C OH R2
2
H
35. A common gaseous fuel that is often found with
In the molecule represented by the formula shown, petroleum is
R could be

A. carbon monoxide B. carbon dioxide

A. CH B. CH2 C. CH3 D. CH4
C. methane D. ethene

31. 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 H H 37. If a hydrocarbon molecule contains a triple bond,
2 2 2 2 its IUPAC name ends with
H C C O C C H
2 2 2 2 A. “ane” B. “ene” C. “one” D. “yne”
H H H H
Which type of compound is represented by the
structural formula shown? 38. What is the maximum number of covalent bonds
that an atom of carbon can form?

A. a ketone B. an aldehyde
A. 1 B. 2 C. 3 D. 4
C. an ester D. an ether

39. Which hydrocarbon formula is also an empirical

formula?

A. CH4 B. C 2 H4 C. C3 H6 D. C4 H8

40. Characteristic Tested Substance

A B C D
High Melting Point X X
Low Melting Point X X
Soluble in Water X X
Insoluble in Water X X
Decomposed under High Heat X
Stable under High Heat X X X
Electrolyte X X
Nonelectrolyte 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. A B. B C. C D. D

41. Given the structural formula for ethyne: 42. What is the name of the compound with the
following formula?
H C C H
H O H
What is the total number of electrons shared 2 2
2 2
between the carbon atoms? H C C C H
2 2
A. 6 B. 2 C. 3 D. 4 H H

A. propanone B. propanol

C. propanal D. propanoic acid

page 5 Organic Chemistry review

43. What is the general formula for an ether? 48. Base your answer(s) to the following question(s)
on the information below.
A. R1 O R2 B. R OH Ethene (common name ethylene) is a
commercially important organic compound.
C. O D. O Millions of tons of ethene are produced by the
2
2 2
2 chemical industry each year. Ethene is used in
R C H R C OH the manufacture of synthetic bers for carpeting
and clothing, and it is widely used in making
polyethylene. Low-density polyethylene can be
44. Which structural formula represents a saturated
stretched into a clear, thin lm that is used for
hydrocarbon?
wrapping food products and consumer goods.
High-density polyethylene is molded into bottles
A. B. 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
C. D. glycol is:

45. Which structural formula represents a saturated

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

C. D. 49. Which formula represents a hydrocarbon?

A. CH3 CH2 CH2 CHO

46. Given the equation: B. CH3 CH2 CH2 CH3

C2 H6 + Cl2 ! C2 H5 Cl + HCl C. CH3 CH2 CH2 COOH

described as 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) 53. H O
on the information below. 2 .
H C C
The hydrocarbon 2-methylpropane reacts
2 /
with iodine as represented by the balanced
H O H
equation below. At standard pressure,
the boiling point of 2-methylpropane Which is an isomer of the compound shown?
is lower than the boiling point of
2-iodo-2-methylpropane.
A. H O
2 .
H C C
2 /
H H

B. H H O
2 2 .
Explain, in terms of bonding, why the hydrocarbon
H C C C
2-methylpropane is saturated.
2 2 /
H H O H
51. Base your answer(s) to the following question(s)
on the information below. C. O
.
Gasoline is a mixture composed H C H
primarily of hydrocarbons such as / 2
isooctane, which is also known as O C H
2,2,4-trimethylpentane. 2
Gasoline is assigned a number called an H
octane rating. Gasoline with an octane rating
D. H H
of 87 performs the same as a mixture that
2 2
consists of 87% isooctane and 13% heptane.
H C C H
An alternative fuel, E-85, can be used 2 2
in some automobiles. This fuel is a mixture
O O
of 85% ethanol and 15% gasoline.
2 2
In the space provided, draw a structural formula H H
for a molecule of 2,2,4-trimethylpentane.

52. 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 O 57. Which structural formula represents an isomer of
2 2 . dimethyl ether?
H C C C
2 2 / A. H O B. H
H H H 2 . 2
Which compound is an isomer of the one shown? H C C H C OH
2 / 2
H H H
A. H H
2 2 C. O D. H H
H C C C H . 2 2
2 2
2 2 H C OH H C C OH
H O H 2 2
H H
B. H H O
2 2 .
H C C C 58. As the number of carbon atoms in a hydrocarbon
2 2 / molecule increases, the number of possible isomers
H H OH generally

C. H H H
2 2 2 A. decreases B. increases
H C C C OH
C. remains the same
2 2 2
H H H

D. H O 59. H H H H
2 . 2 2 2 2
H C C H H C C C C OH
2 2 2 2 2
H H H H H

H H H H
55. Which of the following compounds has the greatest 2 2 2 2
possible number of isomers? H C C C C H
2 2 2 2
H H OH H
A. butane B. ethane
Which is an accurate description of the two
C. pentane D. propane compounds shown?

56. Which is the structural formula for an unsaturated A. They are isotopes of butanol.
compound?
B. They are isomers of butanol.

A. H H B. H C==C
= H C. They are alkanes.
2 2 2 2
D. They are alkenes.
H C C Cl Cl Cl
2 2
H H

C. H H D. H H
2 2 2 2
H C C OH H C O C H
2 2 2 2
H H H H

page 8 Organic Chemistry review

60. H H H 63. H H
2 2 2 2 2
H C C C==O
= H C C OH
2 2 2 2
H H H H
Which structural formula represents an isomer? Which is an isomer of the compound shown?

A. H H H A. H H
2 2 2 2 2
H C C O C H C O C H
2 2 2 2 2
H H H H H

B. H O H B. H H
2 2
2 2 2 2
H C C C H HO C C H
2 2 2 2
H H H H

C. H H H C. H O
2 2 2 2 2
2
H C C C OH H C C H
2 2 2 2
H H H H

D. H H O D. H H H
2 2 . 2 2 2
H C C C H C C O C H
2 2 / 2 2 2
H H OH H H H

61. The isomers CH3 OCH3 and CH3 CH2 OH di er in 64. Which compounds are isomers?

A. molecular formula B. molecular structure A. CH3 OH and CH3 CH2 OH

C. number of atoms D. formula mass B. CH4 and CCl4

C. CH3 CH2 CHO and CH3 COCH3

62. Which compounds are isomers?
D. CH3 CH2 OH and CH3 CH2 COOH

A. CH3 Br and CH2 Br2

B. CH3 OH and CH3 CH2 OH

C. CH3 OH and CH3 CHO

D. CH3 OCH3 and CH3 CH2 OH

page 9 Organic Chemistry review

65. Which formula is an isomer of butane? 67. The reaction CH4 + Br2 ! CH3 Br + HBr is an
example of
A.
A. addition B. hydrogenation

C. substitution D. polymerization

B. 68. Which molecule is represented by X in this

reaction?

H C C H + 2Br2 ! X

A. H H B. H H
2 2 2 2
H C C Br H C C H
2 2 2 2
H H Br Br

C. H H D. Br Br
2 2 2 2
C. H C C Br H C C H
2 2 2 2
H Br Br Br

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

D. of

A. substitution B. polymerization

C. saponi cation D. esteri cation

70. In the reaction shown, what is the formula of the

product represented by the X ?

66. Which is the product of the reaction between H H

ethene and chlorine? / .
C==C
= + Br2 ! X
. /
A. H H B. H H H
2 2 2
H C C Cl H C Cl
2 2 2 A. H H B. H Br
H H H 2 2 2 2
H C C H H C C H
C. H H D. H 2 2 2 2
2 2 2 H H H H
Cl C C Cl Cl C Cl
2 2 2 C. H H D. H C==C
= H
H H H 2 2 2 2
H C C H Br Br
2 2
Br Br

page 10 Organic Chemistry review

71. The process of joining many monomers is called 77. The equation
CH3 OH + CH3 OH ! CH3 OCH3 + H2 O
illustrates the
A. saponi cation B. fermentation

C. polymerization D. substitution A. oxidation of alcohols to form a ketone

B. oxidation of alcohols to form an acid

72. Which are the products of a fermentation reaction?
C. dehydration of alcohols to form a polymer

A. an ester and water D. dehydration of alcohols to form an ether

B. a salt and water

78. Which type of reaction is used in the production
C. an alcohol and carbon dioxide of nylon?
D. a soap and glycerol
A. substitution B. saponi cation

73. In the equation C. esteri cation D. polymerization

CH3 OH + oxidizing agent ! X + H2 O, the
product represented by X is
79. The products of condensation polymerization are
polymer and
A. an alcohol B. an aldehyde

C. an ether D. a ketone A. carbon dioxide B. water

C. ethanol D. glycerol
74. One of the products of condensation polymerization
is
80. Given the equation:
A. water B. an acid C6 H12 O6 ! 2C2 H5 OH + 2CO2
C. a monomer D. a ketone The chemical process illustrated by this equation is

75. Which hydrocarbon will undergo a substitution A. fermentation B. saponi cation

reaction with chlorine
C. esteri cation D. polymerization

A. methane B. ethyne

C. propene D. butene

76. 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
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Organic Chemistry review 05/21/2013

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

39. 53.
Answer: A Answer: C
40. 54.
Answer: B Answer: A
41. 55.
Answer: A Answer: C
42. 56.
Answer: A Answer: B
43. 57.
Answer: A Answer: D
44. 58.
Answer: C Answer: B
45. 59.
Answer: A Answer: B
46. 60.
Answer: C Answer: B
47. 61.
Answer: C Answer: B
48. 62.
Answer: Has a carbon-carbon double bond. Answer: D
49. 63.
Answer: B Answer: A
50. 64.
Answer: A 2-methylpropane molecule has only Answer: C
single carbon-carbon bonds.
65.
There are only single bonds in
methylpropane. Answer: D

no multiple bonds between carbon 66.

atoms Answer: C
51. 67.
Answer: or Answer: C
68.
Answer: D
69.
Answer: B
70.
Answer: C
71.
Answer: C
72.
Answer: C
73.
Answer: B
52. 74.
Answer: propene Answer: A
 Teacher's Key Page 3

75.
Answer: A
76.
Answer: B
77.
Answer: D
78.
Answer: D
79.
Answer: B
80.
Answer: A