Chapter 22 1 Which of the following compounds can exhibit geometrical isomerism

Chapter 22: Organic and Biological Molecules

1. Name the following:

A)

isopropane

B)

methylpentane

C)

methylbutane

D)

n-pentane

E)

dodecane

2. Name the following:

A)

n-heptane

B)

2-methyl-2-ethylbutane

C)

3,3-dimethylpentane

D)

2,2-diethylpropane

E)

none of these

3. Name the following: CH3 –CH2 –CH3

A)

ethane

B)

propane

C)

butane

D)

pentane

E)

hexane

4. Name the following:

A)

2,4-diethylpentane

B)

3,5-dimethylheptane

C)

secondary ethylpentane

D)

2,3-dimethyl-2,3-diethylpropane

E)

none of these

5. Name the following:

A)

n-hexane

B)

isohexane

C)

1,2,3-trimethylpropane

D)

methyl-diethylmethane

E)

3-methylpentane

6. Name the following:

CH3–(CH2)6 –CH3

A)

pentane

B)

hexane

C)

heptane

D)

octane

E)

nonane

7. A student gave a molecule the following name:

2-methyl-4-t-butylpentane

However, the teacher pointed out that, although the molecule could be correctly drawn from

this name, the name violates the IUPAC rules. What is the correct (IUPAC) name of the

molecule?

A)

2-t-butyl-4-methylpentane

B)

2,2,3,5-tetramethylhexane

C)

2,4,5,5-tetramethylhexane

D)

1-sec-butyl-1,2,2-trimethylpentane

E)

none of these

8. Which of the following names is a correct one?

A)

3-methyl-4-isopropylpentane

B)

2-ethyl-4-tertiary-butylpentane

C)

2,2,3,5-tetramethylheptane

D)

t-butylethane

E)

trans-1,2-dimethylethane

9. What is the compound whose carbon skeleton (minus any hydrogen atoms) appears below?

A)

2,4-diethyl-3,6-dimethylheptane

B)

2,5-dimethyl-4,6-diethylheptane

C)

1,4-diethyl-3,6-dimethyl-tridecane

D)

5-ethyl-3,6-trimethyloctane

E)

4-ethyl-2,5,6-trimethyloctane

10. A student gave a molecule the following name: 2-ethyl-3-methyl-5-isopropylhexane

However, his TA pointed out that, although the molecule could be correctly drawn from this

name, the name violates the systematic rules. What is the correct (systematic) name of the

molecule?

A)

3,4-dimethyl-6-isopropylheptane

B)

2-isopropyl-4,5-dimethylheptane

C)

3,4,6,7-tetramethyloctane

D)

1,2-diethyl-3,6,7-trimethylheptane

E)

2,3,5,6-tetramethyloctane

11. In lecture, the professor named a molecule 4-ethylpentane. An alert student pointed out that

although the correct structure could be drawn, the name did not follow systematic rules.

What is the correct systematic name for the molecule?

A)

2-ethylpentane

B)

1-methyl-1-propylpropane

C)

3-methylhexane

D)

4-methylhexane

E)

none of these

12. The compound below is the carbon skeleton (minus any hydrogen atoms) of

Which of these phrases could be used to describe this compound?

I.

C12H26

II.

a substituted octane

III.

a compound with 3 tertiary carbons

IV.

a compound with 3 secondary carbons

V.

a compound with 2 isopropyl groups

A)

I, II, III

B)

II, III, IV

C)

III, IV, V

D)

II, IV, V

E)

I, II, III, IV

13. Which of the following pairs is incorrect?

A)

ethane – C2H4

B)

pentane – C5H12

C)

hexane – C6H14

D)

heptane – C7H16

E)

octane – C8H18

14. Why does octane have a higher boiling point than ethane, 126°C versus –89°C?

A)

Octane exhibits hydrogen bonding and ethane does not.

B)

Octane has a higher vapor pressure than ethane.

C)

Octane contains more double bonds than ethane.

D)

Octane has stronger London dispersion forces than ethane.

E)

At least two of the above are correct.

15. How many isomers of C3H8 are there?

A)

1

B)

2

C)

3

D)

5

E)

6

16. Which is a possible product of the chlorination of butane in the presence of light?

A)

C4H9Cl

B)

C4H8Cl

C)

C4H10Cl2

D)

C4H6Cl2

E)

C4H9Cl2

17. Which of the following, upon reacting with oxygen, would form the greatest amount of

carbon dioxide?

A)

n-pentane

B)

isopentane

C)

neopentane

D)

Two of the above would form equal amounts.

E)

All (A-C) of the above would form equal amounts.

18. Cyclobutane has 109° bond angles like all alkanes.

19. Name the following:

A)

1-hexyne

B)

2-ethynyl butane

C)

2-ethyl-3-butyne

D)

3-methyl-1-pentyne

E)

3-methyl-4-pentyne

20. Name the following:

A)

1,1,1-trichloro-5-bromo-3-pentene

B)

1-bromo-5,5,5-trichloro-2-pentene

C)

1,1,1-trichloro-5-bromo-2-pentene

D)

1,1,1-trichloro-5-bromo-3-pentyne

E)

none of these

21. CH3C  CCH2CH2Cl is named:

A)

1-chloro-3-pentyne

B)

5-chloro-2-pentene

C)

1-acetylenyl-3-chloropropane

D)

5-chloro-2-pentyne

E)

1-chloro-3-pentene

22. One of the ingredients on a margarine container is listed as “polyunsaturated corn oil.” This

means that:

A)

All the carbon bonds in the oil are single bonds.

B)

Many of the polymer bonds are unsaturated.

C)

All the carbon–carbon bonds are triple bonds.

D)

Many of the carbon–carbon bonds are multiple bonds.

E)

None of these.

23. Consider the following four compounds:

Which are the same molecule?

A)

I and II

B)

I and III

C)

II and III

D)

III and IV

E)

I and IV

24. Consider the molecule trans-2-butene. Which statement is true?

A)

The molecule has two  bonds.

B)

There is free rotation around every bond in the molecule.

C)

Cis-2-butene is its structural isomer.

D)

Carbon #2 exhibits sp2 hybridization.

E)

None of the above.

25. Hydrocarbons containing a carbon–carbon triple bond are called

A)

alkynes

B)

alkenes

C)

cyclic alkanes

D)

aldehydes

E)

alkanes

26. How many of the following molecules exist?

I.

methene

II.

cycloethane

III.

cyclopropyne

IV.

neobutane

A)

0

B)

1

C)

2

D)

3

E)

4

27. How many isomers are there of “dichloroethene”?

A)

2

B)

3

C)

4

D)

5

E)

6

28. Propane undergoes dehydrogenation. The product of this is

A)

1-propene

B)

2-propene

C)

cis-1-propene

D)

trans-1-propene

E)

cis-2-propene

29. Chemical reactions involving alkanes in which hydrogen atoms are removed and the product

is an unsaturated hydrocarbon are called

A)

combustion reactions

B)

dehydrogenation reactions

C)

substitution reactions

D)

addition reactions

E)

polymerization reactions

30. Name the following:

A)

2-chloro-3-chloro-cis-2-butene

B)

2,3-dichloro-cis-2-butene

C)

2,3-dichloro-trans-2-butene

D)

1-chloro-1-methyl-2-chloro-propene

E)

2,3-dichloro-1-methyl-propene

31. Which of the following compounds can exhibit geometrical isomerism?

A)

B)

C)

D)

E)

32. How many structural and geometrical isomers are there of chloropropene?

A)

2

B)

3

C)

4

D)

5

E)

more than 5

33. How many geometric isomers can be drawn for the following compound:

CH3CH=CHCH2CH=C(CH3)2

A)

2

B)

3

C)

4

D)

5

E)

6

34. Which of the following is not a structural isomer of 1-pentene?

A)

2-pentene

B)

2-methyl-2-butene

C)

cyclopentane

D)

3-methyl-1-butene

E)

1-methyl-cyclobutene

35. What is the compound represented by the following structure?

A)

cyclohexene, C6H10

B)

cyclohexane, C6H12

C)

cyclohexatriene, C6H9

D)

cyclohexatriene, C6H12

E)

benzene, C6H6

36. How many different possible dimethylbenzenes exist?

A)

2

B)

3

C)

4

D)

5

E)

6

37. What is the most characteristic reaction of benzene?

A)

oxidation

B)

reduction

C)

substitution

D)

addition

E)

addition and elimination

38. Mothballs contain what aromatic hydrocarbon?

A)

naphthalene

B)

benzene

C)

anthracene

D)

phenanthrene

E)

toluene

39. Name the following:

A)

methyl alcohol

B)

ethyl alcohol

C)

propyl alcohol

D)

isopropyl alcohol

E)

butanol

40. Which of the following is known as wood alcohol?

A)

methanol

B)

ethanol

C)

propanol

D)

isopropanol

E)

none of these

41. Which of the following is known as rubbing alcohol?

A)

methanol

B)

ethanol

C)

propanol

D)

isopropanol

E)

none of these

42. What alcohols have the greatest commercial value?

A)

methanol and ethanol

B)

methanol and phenol

C)

ethanol and phenol

D)

1-propanol and ethanol

E)

1-propanol and methanol

43. Which of the following has only one single C-O bond?

A)

ketone

B)

alcohol

C)

ether

D)

ester

E)

aldehyde

44. The boiling point of methanol is much higher than that of ethane. This is primarily due to

A)

the difference in molar masses of methanol and ethane

B)

the hydrogen bonding in methanol

C)

the significant molecular size difference between methanol and ethane

D)

the carbon oxygen double bond in the methanol

E)

none of these

45. Classify the following molecule:

A)

primary alcohol

B)

secondary alcohol

C)

tertiary alcohol

D)

ether

E)

phenol

46. Which of the following is found in beverages such as wine?

A)

methanol

B)

ethanol

C)

propanol

D)

isopropanol

E)

none of these

47. When C4H8 is treated with water and H2SO4, a tertiary alcohol is produced. Which of the

following structures could represent C4H8 in this reaction?

A)

CH3CH=CHCH3

B)

CH3CH2CH=CH2

C)

D)

CH3CH2CH2CH3

E)

none of these

48. Oxidation of a primary alcohol results in a(n) __________ and oxidation of a secondary

alcohol results in a(n) _________.

A)

carboxylic acid, amine

B)

aldehyde, ketone

C)

ester, ether

D)

ketone, aldehyde

E)

amine, carboxylic acid

49. When the following organic compound is oxidized, what is the major organic product?

A)

3-pentanoic acid

B)

3-pentanol

C)

3-pentanone

D)

3-pentanal

E)

No reaction takes place.

50. Name the following:

A)

acetone

B)

butyraldehyde

C)

diethylketone

D)

diethyl ether

E)

none of these

51. Identify the functional group present in the following organic compound:

A)

ester

B)

aldehyde

C)

ether

D)

ketone

E)

none of these

52. Which molecule is an ether?

A)

B)

CH3CH2OCH3

C)

D)

CH3CH2NH2

E)

none of these

53. Name the following:

A)

2-chloro-3-ethyl-1-isopropylbutanone

B)

isopropyl-chloro,methylbutyl ketone

C)

2-butyl,chloro,isobutanoyl methane

D)

4-chloro-2,5-dimethyl-3-heptanone

E)

3-methyl-4-chloro-1-isopropylpentanone

54. Identify the type of organic compound shown:

A)

aldehyde

B)

ester

C)

amine

D)

alcohol

E)

none of these

55. Identify the type of organic compound shown:

A)

aldehyde

B)

ester

C)

amine

D)

ketone

E)

none of these

56. Which molecule is a ketone?

A)

B)

CH3CH2OCH3

C)

D)

CH3CH2NH2

E)

none of these

57. Classify the following molecule:

A)

acid

B)

aldehyde

C)

amine

D)

ketone

E)

carbonyl

58. Classify the following molecule:

A)

acid

B)

aldehyde

C)

amine

D)

ketone

E)

carbonyl

59. Which of the following yields a primary alcohol upon reduction?

A)

a ketone

B)

an alkene

C)

an amine

D)

an aldehyde

E)

an ether

60. Which of the following becomes more soluble in water upon addition of NaOH?

A)

an amine

B)

a carboxylic acid

C)

an aromatic hydrocarbon

D)

an alkane

E)

two of these

61. Which of the following will yield a carboxylic acid upon oxidation?

A)

a secondary alcohol

B)

an aldehyde

C)

a cycloalkane

D)

a ketone

E)

tertiary alcohol

62. What organic molecules have the general formula RCOOH?

A)

esters

B)

alcohols

C)

carboxylic acids

D)

ketones

E)

aldehydes

63. Name the following:

A)

n-propyl acetate

B)

isopropyl formate

C)

isopropyl acetate

D)

ethyl propanoate

E)

none of these

64. What is the common name for acetylsalicylic acid?

A)

orange juice

B)

aspirin

C)

acetone

D)

bananas

E)

vinegar

65. What organic compounds often have pleasant fruity odors?

A)

ethers

B)

alkynes

C)

carboxylic acids

D)

esters

E)

amines

66. Which of the following has a double C-O bond and a single C-O bond?

A)

ketone

B)

ester

C)

alcohol

D)

amide

E)

ether

67. Referring to the structures below, which statement is true?

I.

II.

III.

A)

I and II have different molecular formulas.

B)

I and III are structural isomers of each other.

C)

II and III are stereoisomers of each other.

D)

II and III are different conformations of the same compound.

E)

I and III are the same compound.

68. Identify the type of organic compound shown:

A)

aldehyde

B)

ester

C)

amine

D)

ketone

E)

none of these

69. Which molecule is an ester?

A)

B)

CH3CH2OCH3

C)

D)

CH3CH2NH2

E)

none of these

70. If you were to heat pentanoic acid and 2-butanol with a catalytic amount of strong acid, you

would most likely discover in your flask:

A)

a ketone

B)

an ester

C)

an amine

D)

an alkane

E)

an aldehyde

71. A carboxylic acid will react with an alcohol to form a(n) __________ and a water molecule.

A)

ester

B)

amine

C)

polymer

D)

ketone

E)

aldehyde

72. Aspirin is formed via a(n) __________ reaction.

A)

combustion

B)

hydrogenation

C)

addition

D)

condensation

E)

substitution

73. Which of the following types of compounds must have an sp2-hybridized carbon center?

A)

cyclic ethers

B)

aldehydes

C)

alcohols

D)

alkynes

E)

amines

74. Which of the following functional groups does not contain a doubly bonded oxygen (C=O)?

A)

Aldehyde.

B)

Carboxyl.

C)

Ketone.

D)

Carboxylic acid.

E)

All contain a double bond.

75. H2CCHCH2N(CH3)2 is

A)

an alkyne and a secondary amine

B)

an alkene and a primary amine

C)

an alkene and a tertiary amine

D)

an alkyne and a tertiary amine

E)

none of these

76. Identify the type of organic compound shown: (CH3)3N

A)

aldehyde

B)

ester

C)

amine

D)

ketone

E)

none of these

77. Which molecule is an amine?

A)

B)

CH3CH2OCH3

C)

D)

CH3CH2NH2

E)

none of these