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Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
Quizzes
Quiz 2
Quiz 2
This activity contains 15 questions.
Which of the following would be the least reactive in an S
N
2 reaction?
3-bromoheptane
1-bromo-2-ethylhexane
1-bromo-3-ethylpentane
1-bromo-4-methylhexane
bromocyclohexane
Which of the following statements about an S
N
2 reaction is
not
correct?
It has a unimolecular rate-determining transition state.
The product has an inverted configuration compared to the configuration of the reactant.
Primary alkyl halides are more reactive than tertiary alkyl halides.
It does not involve carbocation rearrangements.
It has a one-step mechanism.
Which of the following represents the correct relative reactivities in an S
N
1 reaction?
3-bromo-3-methylpentane > 2-bromopentane > 1-chloropentane > 2-chloropentane
1-chloropentane > 2-bromopentane > 3-bromo-3-methylpentane > 2-chloropentane
2-bromopentane > 2-chloropentane > 1-chloropentane > 3-bromo-3-methylpentane
3-bromo-3-methylpentane > 2-bromopentane > 2-chloropentane > 1-chloropentane
3-bromo-3-methylpentane > 2-chloropentane > 2-bromopentane > 1-chloropentane
Which of the following statements about an S
N
1 reaction is
not
correct?
Products have both identical and inverted configurations compared with the reactant.
The rate-limiting step has a unimolecular transition state.
The mechanism has one step.
Tertiary alkyl halides are more reactive than secondary alkyl halides.
The reaction can involve carbocation rearrangements.
Which rate equation describes an E2 reaction?
Rate =
k
[alkyl halide]
2
Rate = [alkyl halide][base]
2
Rate = [alkyl halide][base]
Rate = [alkyl halide]
2
[base]
Rate =
k
[alkyl halide]
The E2 reaction is a 1,2-elimination of a proton, H
+
, and a leaving group, Y
-
. In an E2 reaction, how many sigma bonds are there between the proton and the leaving group?
1
2
3
4
5
What product(s) is (are) obtained when 2-bromobutane undergoes an elimination reaction with a strong base?
only 1-butene
only 2-butene
1-butene and 2-butene, with more 2-butene
equal amounts of 1-butene and 2-butene
1-butene and 2-butene, with more 1-butene
Which of the following alkyl halides is the most reactive in an E2 reaction?
CH
2
Br-CH
2
-CH
2
-CH
3
CH
2
Br-CH
3
CH
3
-C(CH
3
)Br-CH(CH
3
)-CH
3
CH
3
-C(CH
3
)Br-CH
2
-CH
3
CH
3
-CHBr-CH
2
-CH
3
Which of the following statements about an E2 reaction is
not
correct?
Tertiary alkyl halides are more reactive than secondary alkyl halides in E2 reactions.
An E2 reaction is a concerted reaction.
If the leaving group is a weak base, C-H bond cleavage is more advanced than C-X bond cleavage.
The rate of an E2 reaction is dependent on the concentrations of the alkyl halide and the base.
If the leaving group is a strong base, C-H bond cleavage is more advanced than C-X bond cleavage.
Which of the following compounds would be the most reactive in an E2 reaction?
6-bromo-1-octene
8-bromo-1-octene
4-bromo-1-octene
5-bromo-1-octene
7-bromo-1-octene
What is the rate-determining step of an E1 reaction?
heterolytic cleavage of the C-X bond to form a carbanion
reaction of the carbocation with a nucleophile
heterolytic cleavage of the C-X bond to form a carbon radical
loss of a proton from the carbocation
heterolytic cleavage of the C-X bond to form a carbocation
Which of the following statements describes the reaction coordinate diagram for an E1 reaction?
a one-step reaction without a transition state
a one-step reaction with two transition states
a one-step reaction with one transition state
a two-step reaction with one intermediate and one transition state
a two-step reaction with one intermediate and two transition states
What is the most likely reaction for a primary halide to undergo in the presence of relatively small base/nucleophile?
S
N
1
E2
E1
S
N
2
E1 and S
N
1
Which of the following is
not
a true statement?
Under S
N
2 and E2 conditions, primary alkyl halides give primarily substitution products.
Under S
N
2 and E2 conditions, tertiary alkyl halides give both substitution and elimination products.
Under S
N
1 and E1 conditions, tertiary alkyl halides give both substitution and elimination products.
Under S
N
1 and E1 conditions, secondary alkyl halides give both substitution and elimination products.
Under S
N
2 and E2 conditions, secondary alkyl halides give both substitution and elimination products.
Which of the following alkyl halides is the most reactive in an E1 reaction?
2-iodo-3-methylbutane
2-iodo-2-methylbutane
2-bromo-3-methylbutane
2-bromo-2-methylbutane
2-chloro-2-methylbutane
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