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Pearson Chemistry Chapter 7

Total questions: 80

Worksheet time: 40mins

Name
Class
Date
1.

What substitution reaction mechanism is most likely for the following compound?

a)

SN1

b)

SN2

c)

Either SN1 or SN2

d)

None of these

2.

Predict the product for the following SN1 reaction.

a)
b)
c)
d)
3.

Consider the following SN2 reaction. Assuming no other changes, what is the effect on rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

a)

It would increase four times

b)

It would reduce by half

c)

It would double the rate

d)

No effect

e)

It would triple the rate

4.

What substitution reaction mechanism is most likely for the following conversion?

a)

SN1

b)

SN2

c)

Either SN1 or SN2

d)

None of these

5.

When drawing a curved arrow mechanism, the head of the arrow goes where?

a)

To the bond that is being broken

b)

To the bond that is being formed

c)

To the source of electrons that is being moved

d)

To the location to which the electrons are being moved

6.

Predict the product for the following reaction.

a)
b)
c)
d)
e)
7.

What is the degree of substitution of the following alkene?

a)

Disubstituted

b)

Trisubstituted

c)

Tetrasubstituted

d)

Monosubstituted

8.

What is the nucleophile in the following reaction?

a)

III

b)

I

c)

II

d)

IV

9.

Predict the product for the following reaction.

a)
b)
c)
d)
e)

None of these

10.

Which of the following alkyl halides will undergo the fastest SN1 reaction?

a)
b)
c)
d)
e)
11.

Which of the following alkyl halides will undergo the fastest SN2 reaction?

a)
b)
c)
d)
e)
12.

Which of the following is an elimination reaction?

a)
b)
c)
d)
13.

Predict the product for the following SN1 reaction.

a)
b)
c)
d)
14.

Predict the product for the following SN2 reaction.

a)
b)
c)
d)
e)
15.

Consider the following SN2 reaction. Assuming no other changes, what is the effect on the rate, if the concentration of NaN3 is tripled?

a)

It would double the rate

b)

It would triple the rate

c)

It would increase the rate six times

d)

No effect

e)

It would increase four times

16.

Which of the following is a weakest nucleophile in a polar protic solvent?

a)

F-

b)

Cl-

c)

Br-

d)

I-

e)

All of these

17.

Predict the product for the following SN2 reaction.

a)
b)
c)
d)
e)

None of these

18.

Predict the product for the following SN1 reaction.

a)
b)
c)
d)
19.

Which of the following is a strongest nucleophile in a polar protic solvent?

a)

F-

b)

Cl-

c)

Br-

d)

I-

e)

None of these

20.

Which of the following is a reasonable definition of a concerted reaction?

a)

A reaction in which bond forming occurs first

b)

A substitution reaction

c)

A reaction in which bond-breaking occurs first

d)

A reaction in which all bond-breaking and bond-forming occurs at the same time

21.

What is the IUPAC name for the following compound?

a)

3,4-Diethyl-6-bromopentane

b)

(2R,4R)-2-Bromo-4,5-diethylheptane

c)

2-Bromo-4-methylhexane

d)

2-Bromo-4-pentylhexane

e)

(2S,4S)-2-Bromo-4,5-diethylheptane

22.

Identify which of the following that is NOT an effect of adrenaline.

a)

Increases heart rate

b)

Makes one sleepy

c)

Provides boost of energy

d)

Increases level of oxygen

e)

Elevates sugar level

23.

Which of the following is a tertiary alkyl halide?

a)

2-Bromo-2-methylpropane

b)

1-Bromo-2-methylpropane

c)

2-Bromopropane

d)

1-Bromobutane

24.

Which of the following is the rate equation for the following SN2 reaction?

a)

Rate = k[1-bromopropane]2[NaCN]2

b)

Rate = k[1-bromopropane] [NaCN]

c)

Rate = k[NaCN]

d)

Rate = k[1-bromopropane]

e)

Rate = k[1-bromopropane]2

25.

Which of the following is most reactive in an E1 reaction?

a)
b)
c)
26.

What is the electrophile in the following reaction?

a)

IV

b)

III

c)

I

d)

II

27.

Consider the following SN2 reaction. Assuming no other changes, what is the effect on the rate, if the concentration of both 1-chloro-3-methylbutane and NaN3 is doubled?

a)

It would increase four times

b)

It would double the rate

c)

No effect

d)

It would triple the rate

e)

It would reduce by half

28.

Rank the following compounds from most to least reactive in an SN2 reaction.

a)

IV > I > II > III

b)

II > I > IV > III

c)

IV > III > I > II

d)

III > IV > I > II

e)

I > IV > II > III

29.

Identify the methylating agent used in biological systems.

a)

Methylproline

b)

Methylalanine

c)

S-adenosylmethionine

d)

Methyl bromide

e)

Methyl iodide

30.

Which of the following is a primary alkyl halide?

a)

(CH3)2CHCH2Cl

b)

(CH3)2CClCH2CH3

c)

(CH3)2CHCHClCH3

d)

(CH3)2CHCH2CCl(CH3)2

31.

Which of the following is a secondary alkyl halide?

a)

1-Bromo-2-methylpropane

b)

1-Bromobutane

c)

2-Bromo-2-methylpropane

d)

2-Bromopropane

32.

Which of the following is a mechanism for an SN2 reaction?

a)

I

b)

III

c)

II

d)

Both I & II

e)

IV

33.

Which of the following is true about the stereochemistry of SN1 reaction?

a)

Inversion of configuration at the electrophilic center

b)

Retention of configuration at the electrophile center

c)

Slightly more retention than inversion at the electrophilic center

d)

Slightly more inversion than retention at the electrophilic center

e)

50:50 mixture of retention and inversion of configuration at the electrophilic center

34.

Which of the following is a strongest nucleophile in a polar protic solvent?

a)

F-

b)

Cl-

c)

OH-

d)

SH-

e)

All of these

35.

The structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol, is shown here. What is the degree of substitution of the alkene in Crestor®?

a)

Monosubstituted

b)

Disubstituted

c)

Trisubstitued

d)

Tetrasubstituted

36.

When drawing a curved arrow mechanism, the tail of the arrow starts where?

a)

The source of electrons that is being moved

b)

The bond that is being formed

c)

The location to which the electrons are being moved

d)

The atom with the positive charge

37.

Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide?

a)
b)
c)
d)
38.

Predict the product for the following reaction.

a)

I & III

b)

IV

c)

I

d)

II

e)

III

39.

Which of the following compounds has the best leaving group?

There needs to be a positive charge on the branch.

a)

I

b)

II

c)

III

d)

IV

e)

All of these

40.

Rank the following compounds from most to least reactive in an SN1 reaction.

a)

III > IV > I > II

b)

IV > III > I > II

c)

II > I > IV > III

d)

IV > I > II > III

e)

I > IV > II > III

41.

What substitution reaction mechanism is most likely for the following conversion?

a)

SN1

b)

SN2

c)

Either SN1 or SN2

d)

None of these

42.

Which of the following is a tertiary alkyl halide?

a)

(CH3)2CHCH2CHClCH2CH3

b)

(CH3)2CHCHClCH3

c)

(CH3)2CHCH2Cl

d)

(CH3)2CClCH2CH3

43.

Which of the following compounds will undergo rearrangement during solvolysis reaction?

a)

3-iodoheptane

b)

3-iodo-3-methylheptane

c)

3-iodo-2-methylheptane

d)

cis-1-iodo-3-methylcyclohexane

e)

3-iodo-5-methylheptane

44.

Which of the following is a substitution reaction?

a)
b)
c)
d)
45.

What is the degree of substitution of the following alkene?

a)

Monosubstituted

b)

Trisubstituted

c)

Tetrasubstituted

d)

Disubstituted

46.

Draw the potential energy diagram for the following SN2 reaction.

a)
b)
c)
d)
e)

None of these

47.

Rank the following compounds from most to least reactive in an SN1 reaction.

a)

I > IV > II > III

b)

I > III > II > IV

c)

IV > III > I > II

d)

III > II > I > IV

e)

II > III > I > IV

48.

Which of the following is not a possible step in a substitution reaction?

a)

II

b)

III

c)

I

d)

IV

49.

What is the degree of substitution of the following alkene?

a)

Tetrasubstituted

b)

Monosubstituted

c)

Disubstituted

d)

Trisubstituted

50.

Rank the following from most to least stable.

a)

II > I > III

b)

III > II > I

c)

I > III > II

d)

II > III > I

e)

I > II > III

51.

What is the electrophile in the following reaction?

a)

I

b)

IV

c)

II

d)

III

52.

Predict the product for the following reaction.

a)

III

b)

I

c)

IV

d)

II

e)

V

53.

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?

a)

Weak nucleophile in a protic solvent

b)

Strong nucleophile in an aprotic solvent

c)

Strong nucleophile in a protic solvent

d)

Weak nucleophile in an aprotic solvent

54.

What substitution reaction mechanism is most likely for the following compound?

a)

SN1

b)

SN2

c)

Either SN1 or SN2

d)

None of these

55.

What is the correct structure for 3-ethyl-1-iodocyclohexane?

a)

IV

b)

III

c)

I

d)

II

56.

Predict the product for the following reaction.

a)

II

b)

III

c)

I

d)

I & II

e)

IV

57.

Draw the transition state for the following SN2 reaction.

a)

III

b)

II

c)

IV

d)

I

58.

Describe a strong nucleophile.

a)

A radical

b)

A cation

c)

An anion

d)

A neutral compound

59.

Which of the following is the correct structure of 4-methylcyclopentene?

a)

I

b)

II

c)

IV

d)

III

60.

Which of the following is the most reactive in an E1 reaction?

a)

I

b)

II

c)

III

61.

Which of the following is the rate equation for the following SN1 reaction?

a)

Rate = k[2-chloro-2-methylpentane] [NaI]

b)

Rate = k[NaI]

c)

Rate = k[Chloride Ion]

d)

Rate = k[2-chloro-2-methylpentane]

62.

Which of the following would be the best base for performing the following elimination?

a)

KOCH3

b)

This reaction is not an elimination reaction

c)

KOCH(CH3)2

d)

KOC(CH3)3

63.

Which of the following is the strongest nucleophile?

a)

III

b)

I

c)

IV

d)

II

64.

What is the IUPAC name for the following compound?

a)

Chlorocyclopentane

b)

2-Chloro-1-methylcyclopentane

c)

1-Chloro-2-methylcyclopentane

d)

1-Methyl-2-chloropentane

65.

Predict the product(s) for the following SN1 reaction.

a)

III

b)

Both I & IV

c)

Both II & III

d)

IV

e)

II

66.

Consider the following SN2 reaction. Assuming no other changes, what is the effect on the rate if the concentration of 1-chloro-3-methylbutane is doubled?

a)

It would increase four times

b)

It would reduce by half

c)

It would double the rate

d)

It would triple the rate

e)

No effect

67.

Which of the following is most likely to act as a base rather than a nucleophile?

a)

III

b)

IV

c)

II

d)

I

68.

Which of the following is NOT a nucleophile?

a)

OH-

b)

NH3

c)

CH3OH

d)

NH4+

e)

All of these

69.

Provide the reagents necessary to carry out the following conversion.

a)

H2O

b)

CH3OH

c)

NaOH in water

d)

NaOH in ether

70.

Which of the following is a substitution reaction?

a)
b)
c)
d)
71.

Which of the following is the correct structure of 2-methyl-1-butene?

a)

II

b)

III

c)

IV

d)

I

72.

The structure of Singulair® (montelukast), a medication used to manage asthma, is shown. What is the degree of substitution of the alkene in Singulair®?

a)

Tetrasubstituted

b)

Monosubstituted

c)

Disubstituted

d)

Trisubstituted

73.

What is the IUPAC name for the following compound?

a)

(S)-2-Fluorobutane

b)

(R)-2-Fluorobutane

c)

2-Fluorobutane

d)

3-Fluorobutane

74.

Which of the following shows a mechanism of a concerted elimination?

a)
b)
c)
d)
75.

Which of the following alkyl halide will undergo the slowest SN1 reaction?

a)
b)
c)
d)
e)
76.

Which of the following is most likely to act as a base rather than a nucleophile?

a)
b)
c)
d)
77.

What set of reaction conditions would favor an SN2 reaction on 2-bromo-3-methylbutane?

a)

Weak nucleophile in an aprotic solvent

b)

Strong nucleophile in an aprotic solvent

c)

Weak nucleophile in a protic solvent

d)

Strong nucleophile in a protic solvent

78.

Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide?

a)

I

b)

III

c)

II

d)

IV

79.

Predict the product for the following SN2 reaction.

a)

III

b)

II

c)

IV

d)

Both I & II

e)

I

80.

Which of the following is the most reactive in an E2 reaction?

a)

I

b)

II

c)

III

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