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Chapter 9 Practice Test

Total questions: 100

Worksheet time: 50mins

Name
Class
Date
1.

When preparing terminal alkynes by an elimination reaction, sodium amide (NaNH2) dissolved in liquid ammonia (NH3) is used most frequently. Which of the following statements offers the best explanation for the above statement?

a)

Sodium amide deprotonates the terminal alkyne, driving formation of the alkynide ion

b)

Only sodium amide is a strong enough base to deprotonate a carbon.

c)

The above statement is false; terminal alkynes are not produced under the given conditions.

d)

Terminal alkynes are more stable than the internal alkynes, and are always the favored product.

e)

Steric hindrance favors preparation of the less substituted terminal alkyne.

2.

Consider the list of alkyne addition reactions below, and select all those that involve an enol intermediate.

a)

Hydroboration/oxidation

b)

HgSO4 catalyzed hydration in dilute H2SO4

c)

Hydrohalogenation

d)

Both Hydroboration/oxidation and HgSO4 catalyzed hydration in dilute H2SO4

e)

Both Hydroboration/oxidation and Hydrohalogenation

3.

Which of the following is the acceptable structure for (R)-5-bromohept-2-yne?

a)

V

b)

I

c)

III

d)

IV

e)

II

4.

Which of the following is the structure for 2-hexyne?

a)

III

b)

IV

c)

II

d)

I

5.

Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr.

a)

1,1-dibromopentane

b)

2-bromo-1-pentene

c)

2,2-dibromopentane

d)

1,2-dibromopentane

e)

1-bromo-1-pentene

6.

Identify the final product for the following reaction.

a)

I

b)

V

c)

III

d)

II

e)

IV

7.

For the reaction shown, select the expected major organic product.

a)

V

b)

I

c)

II

d)

IV

e)

III

8.

Provide the IUPAC name for Cl3CCH2CH2CH2C≡CH.

a)

5,5,5-trichloro-1-pentyne

b)

1-heptyne

c)

1,1,1-trichloro-5-hexyne

d)

6,6,6-trichloro-1-hexyne

e)

trichlorobutylacetylene

9.

Why would the following reaction sequence not produce the expected product shown?

a)

NaNH2 is used in the reduction of alkynes to trans alkenes.

b)

Br is not a good enough leaving group.

c)

The terminal alkyne is not acidic enough to be deprotonated.

d)

The reaction sequence is correct and will produce the shown product.

e)

The secondary alkyl halide would undergo an elimination reaction.

10.

What is the major expected product(s) of the reaction shown below?

a)

2,2-dichloropentane

b)

3,3-dichloropentane

c)

2,3-dichloropentane

d)

2,2-dichloropentane and 3,3-dichloropentane

e)

3,3-dichloropentane and 2,3-dichloropentane

11.

What is the IUPAC name for the molecule shown below?

a)

(E)-5-methyl-5-hepten-1-yne

b)

(E)-3-methyl-2-hepten-6-yne

c)

(Z)-3-methyl-2-hepten-6-yne

d)

(E)-2-butynyl-2-butene

e)

(Z)-5-methyl-5-hepten-1-yne

12.

In an acid-catalyzed hydration, which of the following alkynes is expected to produce a single ketone?

a)

2-decyne

b)

3-decyne

c)

4-decyne

d)

5-decyne

e)

All of the above will give a single product

13.

Provide the IUPAC name for the alkyne expected to produce the two compounds listed below upon ozonolysis.

a)

3-octyne

b)

2,2-dimethyl-3-hexyne

c)

1-tert-butyl-1-butyne

d)

5,5-dimethyl-3-hexyne

e)

3,3-dimethyl-2-hexyne

14.

For the reaction below, select the structure of the major organic product.

a)

III

b)

IV

c)

I

d)

II

e)

V

15.

What is the IUPAC name for the molecule shown below?

a)

3-bromo-4-propyl-5-hexyne

b)

4-ethynyl-5-bromo-heptane

c)

3-bromo-4-acetylenylheptane

d)

4-bromo-3-propyl-1-hexyne

e)

3-(1-bromopropyl)-1-hexyne

16.

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

a)

IV

b)

I

c)

III

d)

V

e)

II

17.

Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

a)

6-bromo-4-hexyne

b)

6-bromo-3-hexyne

c)

1-bromo-3-hexyne

d)

1-bromo-2-hexyne

e)

1-bromo-4-hexyne

18.

For the reaction shown below, the expected product will have a stereochemistry of ______.

a)

achiral

b)

racemic

c)

only (S)

d)

meso

e)

only (R)

19.

For the reaction shown, select the expected major organic product.

a)

II

b)

I

c)

V

d)

IV

e)

III

20.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

a)

A

b)

B

c)

E

d)

D

e)

C

21.

What is the expected major product of the reaction sequence shown below?

a)

IV

b)

I

c)

II

d)

III

e)

V

22.

Identify the final product for the following reaction.

a)

III

b)

V

c)

IV

d)

I

e)

II

23.

For the reaction sequence below, select the expected major product.

a)

3-methyl-1-hexyne

b)

3-methylhexane

c)

3-methyl-2-hexyne

d)

2-bromo-3-methylhexene

e)

1-bromo-3-methylhexene

24.

Rank the following acids in order of decreasing acidity.

a)

V > I > IV > II > III

b)

V > I > III > II > IV

c)

III > IV > II > I > V

d)

I > IV > V > II > III

e)

IV > I > V > II > III

25.

What is the final major product expected for the following reaction sequence?

a)

2,3-dibromo-3-hexene

b)

(R)-3-bromohexane

c)

meso-3,4-dibromohexane

d)

(±)-3,4-dibromohexane

e)

(S)-3-bromohexane

26.

What is the expected major product of the reaction sequence shown below?

a)

CH≡CH + (CH3)2CHC≡CH

b)

(CH3)2CHCH2C≡CH

c)

(CH3)2CHCHBrC≡CH

d)

CH3CHCH2C≡CCH3

e)

(CH3)2CHC≡CCH3

27.

Provide the IUPAC name for HC≡CCH2CH2CH3.

a)

2-butyne

b)

butyne

c)

1-butyne

d)

pentyne

e)

1-pentyne

28.

Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?

a)

III, IV, V

b)

I, II, IV

c)

I and III

d)

II, III, V

e)

II and IV

29.

Which of the following is the structure for 3-sec-butyl-1-heptyne?

a)

IV

b)

I

c)

II

d)

V

e)

III

30.

Which of the following is the structure for 2,5,5-trimethylhept-3-yne?

a)

CH3CH2CH(CH3)C≡CCH2CH(CH3)2

b)

CH3CH2C(CH3)2C≡CCH(CH3)2

c)

CH3CH2CH2CH(CH3)C≡CC(CH3)3

d)

(CH3CH2)2C(CH3)C≡CCH2CH3

e)

CH3CH2C(CH3)2C≡CC(CH3)3

31.

Identify the best reagent(s) for this reaction.

a)

NaOCl

b)

H2SO4, HgSO4, H2O

c)

K2Cr2O7, H+

d)

H2, Pd

e)

1. Disiamylborane, 2. HO-, H2O2

32.

Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of the following compounds?

a)

2,3,4-trimethyl-5-hexyne2

b)

3,4,5-trimethyl-1-hexyne

c)

2,3,4-trimethyl-1-hexene

d)

3,4,5-trimethylhexane

e)

2,3,4-trimethylhexane

33.

A dihalide in which the halogens are attached on the same carbon is called a ________ dihalide.

a)

vicinal

b)

vinylic

c)

cis

d)

allylic

e)

geminal

34.

Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?

a)

1-hexyne

b)

2-hexyne

c)

4-methyl-1-pentyne

d)

3-hexyne

e)

3-methyl-1-pentyne

35.

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

a)

The electronegativity of sp carbons is greater than that of sp2 carbons.

b)

The 4 π electrons of the acetylide anion better stabilize a negative charge.

c)

Acetylide anions are resonance stabilized.

d)

Acetylene has only two hydrogen atoms while ethylene has four.

e)

The electronegativity of sp carbons is less than that of sp2 carbons.

36.

What is the IUPAC name for diisobutylacetylene?

a)

2,7-dimethyl-4-octyne

b)

2,5-diethyl-3-hexyne

c)

2,2,5,5-tetramethyl-3-hexyne

d)

diisopropylbutyne

e)

3,6-dimethyl-4-octyne

37.

The sigma bond of an alkyne is formed from the overlap of which two orbitals?

a)

sp3-sp3

b)

p-p

c)

sp-sp

d)

sp2-sp2

e)

s-s

38.

What are the products of the reaction shown below?

a)

CH3OC≡CH + Na+CH3-

b)

CH3C≡CCH3 + Na+OH-

c)

CH3C≡CH + CH3O-Na+

d)

no reaction

e)

CH3C≡COCH3 + Na+OH-

39.

Identify the major product.

a)

II

b)

IV

c)

I

d)

III

e)

V

40.

What is the IUPAC name for the molecule shown below?

a)

1,1-diethyl-2-pentyne

b)

5-ethyl-3-octyne

c)

5-ethyl-3-heptyne

d)

3-(1-butynyl)pentane

e)

3-ethyl-4-heptyne

41.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

a)

I

b)

V

c)

IV

d)

II

e)

III

42.

Rank the following carbanions in order of increasing base strength.

a)

I < II < III

b)

II < III < I

c)

III < I < II

d)

III < II < I

e)

II < I < III

43.

What is the IUPAC name for the molecule shown below?

a)

5-tert-butyl-1-hexyne

b)

5,6,6-trimethyl-1-heptyne

c)

sec-butyl-tert-butylacetylene

d)

2,2,3-(3-butynyl)butane

e)

2,2,3-trimethyl-6-heptyne

44.

Which of the following statements is true about propyne, H-C≡C-CH3?

a)

The C≡C-C bond angle is 180°.

b)

It contains a total of three pi bonds.

c)

It contains a total of three sigma bonds.

d)

All carbon-carbon bonds are of equal length.

e)

The H-C≡C bond angle is about 109.5°.

45.

What is the IUPAC name for the molecule shown below?

a)

6-bromo-6,6-dimethyl-3-hexyne

b)

6-bromo-3-octyne

c)

6-bromo-6-methyl-3-heptyne

d)

2-bromo-2-methyl-4-heptyne

e)

2-bromo-4-octyne

46.

For the reaction below, select the structure of the expected major organic product.

a)

II

b)

IV

c)

III

d)

I

e)

V

47.

Which sequence of reactions is expected to produce cis-3-octene as the final, and major, organic product?

a)

V

b)

IV

c)

III

d)

I

e)

II

48.

What is the IUPAC name for the molecule shown below?

a)

(E)-5-isopropyloct-5-en-3-yne

b)

(E)-4-isopropyloct-3-en-5-yne

c)

(Z)-5-isopropyloct-5-en-3-yne

d)

(E)-4-(2-methylethyl)oct-3-en-5-yne

e)

(Z)-4-isopropyloct-3-en-5-yne

49.

For the reaction shown, select the expected major organic product.

a)

IV

b)

III

c)

I

d)

V

e)

II

50.

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

a)

IV

b)

I

c)

V

d)

II

e)

III

51.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

a)

B

b)

E

c)

A

d)

D

e)

C

52.

Identify the functional group that would be expected to be found in the final product upon completion of the reaction between 1-hexyne and a mixture of mercuric sulfate and aqueous sulfuric acid.

a)

diol

b)

ketone

c)

ether

d)

carboxylic acid

e)

aldehyde

53.

In the reaction between an alkyne and Na metal in liquid ammonia, the role of Na is an a(n) ___________.

a)

catalyst

b)

Brønsted acid

c)

reducing agent

d)

electrophile

e)

Brønsted base

54.

Provide the IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.

a)

1,1,5,5,5-pentamethyl-2-pentyne

b)

1,1,1,5,5-pentamethyl-3-pentyne

c)

2,6,6-trimethyl-3-heptyne

d)

2,2,6-trimethyl-4-heptyne

e)

tert-butylisopropylacetylene

55.

Identify the final product for the following reaction.

a)

II

b)

IV

c)

III

d)

I

e)

V

56.

What mechanistic intermediate is used to explain the preference for addition of the Br atom, of HBr, to the internal carbon of a terminal alkyne?

a)

Formation of an intermediate with partial positive charge on a secondary carbon

b)

Addition of H, from HBr, to the least hindered carbon.

c)

Steric hindrance for the approach of the Br atom to the primary carbon.

d)

Formation of an intermediate with partial positive charge on a primary carbon

e)

Addition of the H atom to the carbon already with an H.

57.

Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?

a)

H2, Lindlar's catalyst

b)

2 moles of HCl

c)

Na, NH3(I)

d)

2 moles H2, Pt

e)

1 mole H2, Pt

58.

For the reaction shown below, the resulting stereochemistry of the expected product is best described as:

a)

only (S)

b)

(S,Z)

c)

(S,E)

d)

(R,Z)

e)

(R,E)

59.

Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of Br2.

a)

1,1-dibromo-1-pentene

b)

(E)-1,2-dibromo-1-pentene

c)

(Z)-1-bromo-1-pentene

d)

1,1-dibromo-1-pentene and (E)-1,2-dibromo-1-pentene

e)

(E)-1,2-dibromo-1-pentene and (Z)-1-bromo-1-pentene

60.

Identify the final product for the following reaction.

a)

I

b)

V

c)

III

d)

II

e)

IV

61.

For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?

a)

II

b)

III

c)

I

d)

V

e)

IV

62.

Which of the following is the structure for (2E,4E)-octa-2,4-dien-6-yne?

a)

V

b)

II

c)

IV

d)

I

e)

III

63.

What is the final major product expected for the following reaction sequence?

a)

2,3-dichloro-3-hexene

b)

(±)-3,4-dichlorohexane

c)

meso-3,4-dichlorohexane

d)

(S)-3-chlorohexane

e)

(R)-3-chlorohexane

64.

What is the expected major final product of the reaction sequence shown below?

a)

I

b)

IV

c)

None of the shown products will be produced

d)

II

e)

III

65.

Which of the circled hydrogen atoms is the most acidic?

a)

II

b)

V

c)

I

d)

III

e)

IV

66.

Provide the IUPAC name for Cl3C(CH2)4C≡CH.

a)

7,7,7-trichloro-1-heptyne

b)

4,4,4-trichloro-1-butyne

c)

6,6,6-trichloro-1-hexyne

d)

1,1,1-trichloro-5-heptyne

e)

1,1,1-trichloro-6-heptyne

67.

What is the IUPAC name for the molecule shown below?

a)

(2E,4R)-4-chlorohept-2-en-5-yne

b)

(2E,4S)-4-chlorohept-2-en-5-yne

c)

(4S,5E)-4-chlorohept-5-en-2-yne

d)

(4R,5Z)-4-chlorohept-5-en-2-yne

68.

Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-pentene?

a)

HgSO4, H2O

b)

excess HCl

c)

H2, Lindlar's catalyst

d)

Na, NH3

e)

H2, Pt

69.

Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne?

a)

IV

b)

I and II are both correct

c)

II

d)

III

e)

I

70.

Which of the circled hydrogen atoms is the least acidic?

a)

V

b)

IV

c)

I

d)

III

e)

II

71.

Predict the major organic products of the reaction below.

a)

I and II

b)

II and IV

c)

I and III

d)

I and IV

e)

II and III

72.

A dihalide in which the halogens are attached on adjacent carbons is called a ______ dihalide.

a)

Geminal

b)

Vinylic

c)

Vicinal

d)

Allylic

e)

Cis

73.

For the reaction below, how many different organic products would be expected?

a)

Three

b)

One

c)

Two

d)

Four

e)

Five

74.

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

a)

I

b)

IV

c)

V

d)

II

e)

III

75.

For 2-pentyne, which of the following describes the orbital overlap of the C2-C3 sigma bond?

a)

sp3-sp3

b)

p-p

c)

sp3-sp

d)

sp2-sp2

e)

sp-sp

76.

What is the IUPAC name for the expected product of the reaction below?

a)

(E)-3-hexyne

b)

1-hexyne

c)

2-hexyne

d)

3-hexyne

e)

propyne

77.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

a)

B

b)

A

c)

C

d)

E

e)

D

78.

Select the reagent(s) expected to accomplish the reaction shown below.

a)

H2, Pd

b)

H2, Lindlar's catalyst

c)

Na, NH3(l)

d)

H2, Pd and H2, Lindlar's catalyst

e)

H2, Lindlar's catalyst and Na, NH3(l)

79.

What is the IUPAC name for the molecule shown below?

a)

4-tert-butyl-2-pentyne

b)

2,2,3-trimethyl-4-hexyne

c)

4,5,5-trimethyl-2-hexyne

d)

2,2-dimethyl-3-(1-propynyl)butane

e)

4,5,5,5-tetramethyl-2-pentyne

80.

Identify the product of the reaction of an alkyne with sodium and ammonia.

a)

alkane

b)

diene

c)

cis alkene

d)

trans alkene

e)

alkyne

81.

For the reaction shown, select the expected major organic product.

a)

V

b)

IV

c)

II

d)

III

e)

I

82.

Give the hybridization for the carbanion in the acetylide ion.

a)

s2p2

b)

sp3

c)

sp

d)

sp2

e)

s2p

83.

For the reaction shown below, select the expected major product.

a)

II

b)

V

c)

I

d)

III

e)

IV

84.

Which sequence of reagents would be expected to accomplish the synthesis of 1-butyne shown below?

a)

C

b)

E

c)

B

d)

A

e)

D

85.

Identify the final product for the following reaction.

a)

III

b)

IV

c)

V

d)

II

e)

I

86.

What is the IUPAC name for the molecule shown below?

a)

5,5,5-trichloro-2-pentyne

b)

1,1,1-trichloro-4-hexyne

c)

6,6,6-trichloro-2-hexyne

d)

4,4,4-trichloro-1-butyne

e)

1,1,1-trichloro-2-butyne

87.

What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure?

a)

sp3, sp2

b)

sp, sp

c)

sp2, sp

d)

sp, sp2

e)

sp2, sp2

88.

Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

a)

2-hexyne

b)

cis-2-hexene

c)

cis-3-hexene

d)

trans-2-hexene

e)

3-hexyne

89.

What is the expected functional group produced when cyclodecyne is reacted with disiamylborane, followed with treatment of basic hydrogen peroxide?

a)

aldehyde

b)

ether

c)

carboxylic acid

d)

diol

e)

ketone

90.

Select the best explanation for why methanol, CH3OH, cannot be used as a solvent for the deprotonation of a terminal alkyne by sodium amide, NaNH2.

a)

Methanol is more acidic than the alkyne and will be deprotonated instead.

b)

Sodium amide is not a strong enough base to deprotonate the alkyne.

c)

Sodium amide in methanol reduces alkynes to alkenes.

d)

Methanol is toxic, and should be avoided when possible.

e)

Methanol is a poor solvent for dissolving alkynes.

91.

Identify the expected major product from the treatment of 1-pentyne with 1 equivalent of HBr.

a)

2,2-dibromopentane

b)

2-bromo-1-pentene

c)

1,2-dibromopentane

d)

1-bromo-1-pentene

e)

1,1-dibromopentane

92.

Sodium amide (NaNH2, sodamide) reacts with terminal alkynes as a ____.

a)

Brønsted acid

b)

Brønsted base

c)

reducing agent

d)

electrophile

e)

catalyst

93.

What is the IUPAC name for the molecule shown below?

a)

5-ethyl-2-methyl-3-octyne

b)

1-isopropyl-3-ethyl-1-hexyne

c)

2-methyl-5-propyl-3-heptyne

d)

6-methyl-3-propyl-4-heptyne

e)

4-ethyl-7-methyl-5-octyne

94.

For the reaction shown, select the expected major organic product.

a)

II

b)

I

c)

IV

d)

III

e)

V

95.

Which of the reagents below would convert 2-pentyne to trans-2-pentene?

a)

NaNH2, NH3

b)

H2, Lindlar's catalyst

c)

H2, Pd/C

d)

H2O, HgSO4/H2SO4

e)

Na, NH3

96.

How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne, in the presence of a palladium catalyst?

a)

2

b)

3

c)

6

d)

8

e)

1

97.

For 2,4-hexadiyne, which of the following describes the orbital overlap of the C3-C4 sigma bond?

a)

sp2-sp2

b)

sp3-sp3

c)

sp3-sp

d)

sp-sp

e)

p-p

98.

How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?

a)

5

b)

4

c)

2

d)

3

e)

1

99.

The major result of treating 1-butyne with 6M aqueous NaOH would be:

a)

nothing, as the alkyne would not react to an appreciable extent.

b)

the production of an enol.

c)

the production of an alkene.

d)

the production of an alkane.

e)

the production of the sodium alkynide.

100.

Which of the following statements best describes the general reactivity of alkynes?

a)

Alkynes fail to undergo electrophilic addition reactions, unlike alkenes.

b)

An alkyne reacts as an electrophile and is therefore electron rich.

c)

An alkyne reacts as a nucleophile and is therefore electron poor.

d)

An alkyne reacts as an electrophile and is therefore electron poor.

e)

An alkyne reacts as a nucleophile and is therefore electron rich.

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