Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
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2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
Single Jeopardy Answers
1. SN2 Rxns
Answer
50
SN2 reactions proceed best with this type of
substrate.
100 SN2 reactions are much faster in these types
of solvents.
150 SN2 reactions are only possible with carbons
that have this type of hybridization.
200 SN2 reactions are faster when this component
of the reaction mixture is small.
250 SN2 substrates undergo this unique
phenomenon during their transition states.
2. SN1 Rxns
Pts Answer
50 SN1 reactions are fastest with this type of
substrate.
100 SN1 reactions form these as part of their
mechanism.
150 SN1 reactions are faster in this type of
solvent.
200 SN1 reactions are often undesirable because
they destroy this desirable quality in the
starting material.
250 This is the term used to describe SN1 product
mixtures, in which both enantiomers of the
product molecule are present.
Questions
Questions
3. E2 Rxns
Pts Answer
Questions
50 The rate of E2 is highest when a nucleophile
has this quality.
100 E2 reactions are characterized by this type of
reaction order.
150 This type of carbon hybridization is found in
the product molecules of E2 reactions.
200 Mechanisms of the type found in E2
reactions, in which the entire process happens
in one step, are said to be this.
250 E2 reactions normally, but not always,
depend on the following stereochemical
relationship.
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2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
4. E1 Rxns
Pts Answer
Questions
50 E1 reactions convert alkyl halides to this
functional group.
100 The rate determining step in E1 reactions is
the same as that in this type of reaction.
150 E1 reactions are characterized by this type of
reaction order.
200 The rate of E1 is highest when the solvent
present has this quality.
250 The nature of this component has no effect on
the rate of E1 reactions.
5. Between Us
Pts Answer
50 Increasing the concentration of a strong base
in the reaction mixture will cause the
mechanism to shift from an E1 to this type of
reaction.
100 Use a polar protic solvent, a good leaving
group, and limit the basicity of the
nucleophile to shift the product mixture to
this type of product rather than an SN2.
150 Big, bulky bases are likely to make a reaction
proceed by this mechanism rather than an
SN2.
200 A tertiary substrate with beta carbon
branching in the presence of a weak, bulky
nucleophile should favor this mechanism
rather than SN1.
250 This is the most important predictor of
whether a reaction proceeds primarily by SN1
or SN2.
6. Solvents
Pts Answer
50
Polar protic solvents are necessary for E1 and
SN1 reactions because they facilitate this
initial step.
100 A change in solvent can alter this quality of
the halides.
150 These two types of substrates can not react
with the solvents in which they are placed
(i.e. they do not undergo solvolysis
reactions).
200 Acetone, DMF, and DMSO are solvents
which favor this type of reaction.
250 These types of solvents are very poor
ionizers.
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Questions
Questions
2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
Double Jeopardy Answers
1. Solvents
Pts Answer
Questions
100 An example of a common polar protic solvent
is _____.
200 Polar protic solvents are necessary for E1 and
SN1 reactions because they facilitate the
initial step.
300 A change in solvent can alter this quality of
the halides.
400 The absence of a solvent means these 2 types
of reactions do not occur in the gas phase.
500 An example of solvent in which an SN1
reaction will never occur is ______.
2. Why N.R.?
Pts Answer
100
Questions
Cl
CH3OH
CH3CH2
200
CH3CH2
OCH3
CH3CH2
NaBr
C OCH3
CH3CH2
300
CH3CH2
CH3OH
C Br
CH3CH2
NaBr
CH3
CN
CH3
Br
CH3OH
400
Me4N Br
OTs
500
Br
Br
hexane
+ HC CH
CH
+
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HBr
2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
3. Rxn Types
Pts
100
200
300
400
500
Answer
Is an example of this type of reaction, in
which a substrate reacts with its solvent.
When this type of reaction is exothermic, it
will proceed before any others.
The stereochemical consequence of this type
of reaction is likely to be a racemic mixture.
This type of reaction results is stereochemical
inversion.
This type of reaction can occur with primary,
secondary, and tertiary substrates.
Questions
4. Carbocations
Pts Answer
100 When you see a carbocation, the three things you must
immediately consider.
200 Writing this type of carbocation on an exam is suicide.
300 Of secondary, allylic, and benzylic substrates, this
substrate forms the most energectically favorable
carbocation.
400 Saturated carbocations are stabilized by this
phenomenon.
500
Questions
The reason the first carbocation is
lower in E than the other two.
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2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
5. Well, Poor, N.R.
Pts Answer
100
CH3
Questions
H3C C CH2CH2CH2CH2OH
CH3SO2O
CH3NO2
O
200
Br
OH
NaOH
O
300
I
SCH3
NaSCH3
CH3OH
400
NaOEt
Cl
500
EtOH
CH3I
O
O
I
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2/16/2016
Organic Chemistry, Game 17: Substitution and Elimination Reactions
(based on Volhardt and Schore, 3rd edition, Chapter 7)
6. Kinetics
Pts Answer
100
Questions
The figure is a reaction
coordinate diagram that belongs
to this type of reaction.
200
The figure is a reaction
coordinate diagram that belongs
to this type of reaction.
300 The SN2, E2, SN1, and E1 reactions undergo this type of
control, which means that, when a reaction can go by more than
one mechanism, the major product forms from the mechanism
whose transition state energy is the lowest.
400 Reactions that follow this kinetic order, in which the
concentration of only one reagent determines the entire rate
law, are said to be this.
500 A reaction with a transition state energy higher than this
amount is unfavorable under normally available laboratory
conditions.
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