Clicker Questions
Chapter 9
Substitution and
Elimination
Reactions of Alkyl
Halides
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What happens in the following SN2
reaction if the concentration of both
reagents is doubled?
A. The reaction rate doubles.
B. The reaction rate triples.
C. The reaction rate is quadrupled.
D. The reaction rate is unaffected.
E. The reaction rate is halved.
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What happens in the following SN2
reaction if the concentration of both
reagents is doubled?
A. The reaction rate doubles.
B. The reaction rate triples.
C. The reaction rate is quadrupled.
D. The reaction rate is unaffected.
E. The reaction rate is halved.
rate = k2[halide][nucleophile]
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Which of the following factors favor
an SN2 reaction with a negatively
charged nucleophile?
A. a good leaving group
B. a good nucleophile
C. an unhindered reaction center
D. an aprotic polar solvent
E. all of the above
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Which of the following factors favor
an SN2 reaction with a negatively
charged nucleophile?
A. a good leaving group
B. a good nucleophile
C. an unhindered reaction center
D. an aprotic polar solvent
E. all of the above
The rate of an SN2 reaction is
dependent upon all of these factors.
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Which of the following species is
the best nucleophile in methanol?
A. F−
B. NH3
C. CH3S−
D. CH3O−
E. HO−
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Which of the following species is
the best nucleophile in methanol?
A. F−
B. NH3
C. CH3S−
D. CH3O−
E. HO−
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In a protic solvent,
nucleophilicity
increases down a
column.
Which of the following substrates
react fastest in an SN2 reaction?
A. vinyl bromide
B. cyclohexyl bromide
C. phenyl iodide
D. 2-bromopropane
E. benzyl bromide
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Which of the following substrates
react fastest in an SN2 reaction?
A. vinyl bromide
B. cyclohexyl bromide
C. phenyl iodide
D. 2-bromopropane
E. benzyl bromide
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The alkyl halide is
primary.
Vinyl bromide and
phenyl iodide do not
undergo SN2 reactions
Which of the following best
explains a partial racemization?
A. a good leaving group
B. an SN2 reaction
C. formation of an intimate ion pair
D. completely dissociated ions
E. a polar solvent
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Which of the following best
explains a partial racemization?
A. a good leaving group
B. an SN2 reaction
C. formation of an intimate ion pair
D. completely dissociated ions
E. a polar solvent
The leaving group must be fully dissociated for
complete racemization to occur in an SN1 reaction.
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Which of the following statements is not
true about the SN1 reaction of an alkyl
halide?
A. Tertiary alkyl halides and benzyl and allyl halides
undergo SN1 reactions.
B. The rate is dependent upon the stability of the
carbocation.
C. The rate is dependent upon the concentration of
the nucleophile.
D. The reaction requires a good leaving group.
E. The reaction is favored in a polar protic solvent.
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Which of the following statements is not
true about the SN1 reaction of an alkyl
halide?
A. Tertiary alkyl halides and benzyl and allyl halides
undergo SN1 reactions.
B. The rate is dependent upon the stability of the
carbocation.
C. The rate is dependent upon the concentration of
the nucleophile.
D. The reaction requires a good leaving group.
E. The reaction is favored in a polar protic solvent.
The rate-determining step is formation of the
carbocation, which is independent of the nucleophile.
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Which of the following statements
is false?
A. Increasing solvent polarity decreases the reaction rate
when any reactant is charged.
B. Increasing solvent polarity increases the reaction rate
when none of the reactants is charged.
C. An E2 reaction is favored by a high concentration of a
strong, hindered base.
D. An E1 reaction is favored by a secondary alkyl
halide.
E. An E2 is favored by a strong base.
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Which of the following statements
is false?
A. Increasing solvent polarity decreases the reaction rate
when any reactant is charged.
B. Increasing solvent polarity increases the reaction rate
when none of the reactants is charged.
C. An E2 reaction is favored by a high concentration of a
strong, hindered base.
D. An E1 reaction is favored by a secondary alkyl
halide.
E. An E2 is favored by a strong base.
Secondary alkyl halides do not undergo
SN1/E1 solvolysis reactions.
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Which of the following compounds
undergoes an E2 reaction most
readily?
A.
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B.
C.
D.
E.
Which of the following compounds
undergoes an E2 reaction most
readily?
A.
B.
C.
D.
E.
Only in D are both substituents to be eliminated in
axial positions.
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Which of the following bases most
favors elimination over substitution?
H2O
A.
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CH3O− (CH3)3CO− CN−
B.
C.
D.
CH3S−
E.
Which of the following bases most
favors elimination over substitution?
H2O
A.
CH3O− (CH3)3CO− CN−
B.
C.
D.
CH3S−
E.
A strong, bulky base favors elimination over
substitution.
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Which alkyl halide reacts the
fastest with sodium methoxide
under E2 conditions?
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A.
B.
D.
E.
C.
Which alkyl halide reacts the
fastest with sodium methoxide
under E2 conditions?
A.
D.
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B.
E.
C.
I− is the best leaving
group, and E has eight
hydrogens that can
readily be removed by
a strong base.
In the following reaction, which
base most favors the anti-Zaitsev
product?
A.
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B.
C.
D.
E.
In the following reaction, which
base most favors the anti-Zaitsev
product?
A.
B.
C.
D.
E.
The most sterically hindered base favors anti-Zaitsev
elimination.
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