1

Chapter 8. Alkene: Elimination Reactions

Junha Jeon
Department of Chemistry
University of Texas at Arlington
Arlington, Texas 76019

Chem 2321, Fall 13
8.1 Elimination Reactions
! 1,2-elimination
Elimination Reactions
! The reaction produces the alkene product and HBr; called
dehydrohalogenation.
Elimination Reactions
Elimination reactions often compete with substitution reactions.
What are the two main ingredients for a substitution?
A nucleophile and an electrophile with a leaving group
What are the two main ingredients for an elimination?
A base and an electrophile with a leaving group
How is a base both similar and different from a nucleophile?
Elimination Reactions
Elimination reactions often compete with substitution reactions.
What are the two main ingredients for a substitution?
A nucleophile and an electrophile with a leaving group
What are the two main ingredients for an elimination?
A base and an electrophile with a leaving group
How is a base both similar and different from a nucleophile?
Elimination Reactions
Elimination reactions often compete with substitution reactions.
What are the two main ingredients for a substitution?
A nucleophile and an electrophile with a leaving group
What are the two main ingredients for an elimination?
A base and an electrophile with a leaving group
How is a base both similar and different from a nucleophile?
2
Elimination Reactions
Elimination reactions often compete with substitution reactions.
What are the two main ingredients for a substitution?
A nucleophile and an electrophile with a leaving group
What are the two main ingredients for an elimination?
A base and an electrophile with a leaving group
How is a base both similar and different from a nucleophile?
Ethylene and Propylene
Ethylene and Propylene Ethylene and Propylene
Ethylene and Propylene Ethylene and Propylene
3
Ethylene and Propylene Ethylene and Propylene
8.2 Alkenes: Nomenclature by IUPAC
Recall:
1. Leaving groups: Identify and name the parent chain.
2. Identify the name of the substituents (side groups).
3. Assign a locant (number) to each substituent.
4. Assemble the name alphabetically.

Alkenes: Nomenclature by IUPAC
Recall:
1. Leaving groups: Identify and name the parent chain.
2. Identify the name of the substituents (side groups).
3. Assign a locant (number) to each substituent.
4. Assemble the name alphabetically.

Alkenes: Nomenclature by IUPAC
Recall:
1. Leaving groups: Identify and name the parent chain.
2. Identify the name of the substituents (side groups).
3. Assign a locant (number) to each substituent.
4. Assemble the name alphabetically.

Alkenes: Nomenclature by IUPAC
Recall:
1. Leaving groups: Identify and name the parent chain.
2. Identify the name of the substituents (side groups).
3. Assign a locant (number) to each substituent: Give the C=C double bond
the lowest number possible.
4. Assemble the name alphabetically.

4
Alkenes: Nomenclature by IUPAC
Recall:
1. Leaving groups: Identify and name the parent chain.
2. Identify the name of the substituents (side groups).
3. Assign a locant (number) to each substituent: Give the C=C double bond
the lowest number possible.
4. Assemble the name alphabetically.

Alkenes: Common Names
Alkenes: Common Names The Degree of Substitution
Stability of Alkenes Stereoisomerism in Alkenes: Not Exhibiting Free Rotation
5
Stereoisomerism in Alkenes Stereoisomerism in Alkenes
Bredts rule:
A bridgehead carbon of a bicyclic system cannot possesses a C=C double bond if it
involves a trans pi-bond being incorporated in a small ring.
Stereoisomerism in Alkenes: Not Exhibiting Free Rotation E and Z Designations
E and Z Designations
1.Prioritize the groups attached to the C=C double bond based on atomic number.
2.If the top priority groups are on the same side of the C=C double bond, it is Z
(for zusammen, which means together).
3.If the top priority groups are on opposite sides of the C=C double bond, it is E
(for entgegen, which means opposite).

E and Z Designations
1.Prioritize the groups attached to the C=C double bond based on atomic number.
2.If the top priority groups are on the same side of the C=C double bond, it is Z
(for zusammen, which means together).
3.If the top priority groups are on opposite sides of the C=C double bond, it is E
(for entgegen, which means opposite).

6
8.5 Alkene Stability
Because of steric strain, cis isomers are generally less stable than trans.

Stability Measurement: Heat of Combustion
Relative Stability: Isomeric Alkenes Stability: Electron Donation of Alkyl Hyperconjugation
The delocalization of electron
density by hyperconjucation
is stabilizing effect!
8.6 Elimination Reactions Recall Four Patterns
7
Two Patterns in Elimination Reactions
E2: A concerted mechanism
E1: A stepwise mechanism
Two Patterns in Elimination Reactions
E2: A concerted mechanism
E1: A stepwise mechanism
Two Patterns in Elimination Reactions
E2: A concerted mechanism
E1: A stepwise mechanism
8.7 E2
E2: A concerted mechanism
E2: Example
E2: A concerted mechanism
E2: Example
E2: A concerted mechanism
8
E2: Kinetics
E2: A concerted mechanism
The kinetics of E2 and S
N
2 are quite similar!
E2
E2: A concerted mechanism
E2: Effect of Substrate
Tertiary substrates are unreactive toward
S
N
2 while they react readily by E2.
E2: Effect of Substrate
! ! !
E2: Effect of Substrate E2: Energy Diagram
Look at TS-->
9
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
Stability: Electron Donation of Alkyl Hyperconjugation
The delocalization of electron
density by hyperconjucation
is stabilizing effect!
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
H
H
H
H
H
H
H
3
C
H
3
C
H
H
H
H
3
C (1) (2)
(3)
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
H
H
H
H
H
H
H
3
C
H
3
C
H
H
H
H
3
C (1) (2)
(3)
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
H
H
H
H
H
H
H
3
C
H
3
C
H
H
H
H
3
C (1) (2)
(3)
10
E2: Transition State
! The 3 substrate should proceed through a more stable transition state
(kinetically favored) and a more stable product (thermodynamically favored).
H
H
H
H
H
H
H
3
C
H
3
C
H
H
H
H
3
C (1) (2)
(3)
E2: Not Very Sensitive to Steric Hindrance#

E2: Regioselectivity E2: Regioselectivity
E2: Regioselectivity Sterically Less Hindered Bases
! Zaitsev product: the more substituted alkene
! Hofmann product: the less substituted alkene
E2: Regioselectivity Sterically Hindered Bases
The regiochemistry of the E2 reaction can be controlled by choosing the base.
11
E2: Regioselectivity Sterically Hindered Bases
Examples of bulky bases
E2: Stereoselectivity E/Z Selection
E2: Stereoselectivity E/Z Selection Recall Hammond Postulate E2: Stereospecicity
Only product
No other possible stereoisomers
E2: Stereospecicity
! To rationalize the stereospecicity of the reaction, consider the alignment of
the orbitals in the transition state for the reaction.
! In the transition state, the CH and CBr bonds that are breaking must be
rotated into the same plane as the pi bond that is forming.
E2: Stereospecicity
12
E2: Stereospecicity E2: Stereospecicity
E2: Stereospecicity
! Evidence suggests that a strict 180 angle is not necessary for E2
mechanisms.
! Similar angles (175-179) are sufcient.
! The term, anti-periplanar is generally used instead of anti-coplanar to account
for slight deviations from coplanarity.

Anti-Periplanar

The stereoisomeric product of an E2 process depends on the conguration

of the starting alkyl halide.
E2: Stereospecicity
! Evidence suggests that a strict 180 angle is not necessary for E2
mechanisms.
! Similar angles (175-179) are sufcient.
! The term, anti-periplanar is generally used instead of anti-coplanar to account
for slight deviations from coplanarity.

Anti-Periplanar

The stereoisomeric product of an E2 process depends on the conguration

of the starting alkyl halide.
E2: Stereospecicity Anti-Periplanar E2: Stereospecicity Anti-Periplanar
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E2: Stereospecicity
Cl
Base
+ HBase 1.
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me
+
Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

Due by next Tuesday

Cl
Base
+ HBase 1.
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me
+
Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

Cl
Base
+ HBase 1.
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me
+
Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

Cl
Base
+ HBase 1.
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me
+
Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

+
14
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

+
Cl
Base
+ HBase 2.
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Me Me Me
Cl Me Cl Me
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

+
The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Cl Me Cl Me
vs.
Neomenthyl chloride Menthyl chloride
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

The rate of E2 reaction is greatly affected by the

amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Cl Me Cl Me
vs.
Neomenthyl chloride Menthyl chloride
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

200 more reactive

The rate of E2 reaction is greatly affected by the
amount of time that the leaving group spends in
an axial position. Which is more reactive?
3.
Cl Me Cl Me
vs.
Neomenthyl chloride Menthyl chloride
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar

to the board
200 more reactive
Due by next Tuesday
8.8 E2: Acyclic Substrate
15
8.8 E2: Acyclic Substrate with the Less Sterically Hindered Base 8.8 E2: Acyclic Substrate Newman Projection Is Helpful!
8.8 E2: Acyclic Substrate Newman Projection Is Helpful! 8.8 E2: Acyclic Substrate Newman Projection Is Helpful!
Zaitsev Hofmann
8.9 E1
cf. slide 32 (E2)
8.9 E1
16
E1 E1
E1 E1
E1: 1. Effect of Substrate Similar with S
N
1 E1: 1. Effect of Substrate
Because E1 and S
N
1 proceed by the same rst step, their competition will
generally result in a mixture of products
17
E1: 1. Effect of Substrate
Because E1 and S
N
1 proceed by the same rst step, their competition will
generally result in a mixture of products
E1: 2. Regioselectivity Compare to E2
The regiochemical outcome of an E2 reaction can be controlled by the base
(sterically hindered or not sterically hindered)

E1. Regioselectivity Generally the Zaitsev Product

Generally E1 gives the more substituted alkene (Zaitsev product)

E1 reactions are not stereospecic that is, they are not required anti-periplanarity
in order for the reaction to occur.
Nevertheless, E1 reactions are stereoselective (E vs Z).
E1. Regioselectivity Generally the Zaitsev Product
Generally E1 gives the more substituted alkene (Zaitsev product)

E1 reactions are not stereospecic that is, they are not required anti-periplanarity
in order for the reaction to occur.
Nevertheless, E1 reactions are stereoselective (E vs Z).
E1. Regioselectivity Generally the Zaitsev Product
Generally E1 gives the more substituted alkene (Zaitsev product)

E1 reactions are not stereospecic that is, they are not required anti-periplanarity
in order for the reaction to occur.
Nevertheless, E1 reactions are stereoselective (E vs Z).
E1. 3. Drawing the Mechanism
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E1. 3. Drawing the Mechanism
S
N
1 process
E1 process
E1. 3. Drawing the Mechanism
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
19
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
20
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
E1. 3. Drawing the Mechanism E1. 3. Drawing the Mechanism
In fact,
E1. 3. Drawing the Mechanism
In fact,
8.11 E2: Drawing the Mechanism
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8.12 Substitution vs. Elimination#

Substitution and elimination are always in competition.
Sometimes, products are only observed from either substitution or
elimination.
Sometimes a mixture of products is observed.

Substitution vs. Elimination#

Substitution and elimination are always in competition.
Sometimes, products are only observed from either substitution or
elimination.
Sometimes a mixture of products is observed.

Substitution vs. Elimination#

Substitution and elimination are always in competition.
Sometimes, products are only observed from either substitution or
elimination.
Sometimes a mixture of products is observed.

8.12 Substitution vs. Elimination#

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
22
Substitution vs. Elimination: Reagent

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Determine the function of the reagent: assess the strength of a nucleophile:
! The greater the negative charge, the more nucleophilic it is likely to be.
! The more polarizable it is, the more nucleophilic it should be.
! The less sterically hindered it is, the more nucleophilic it should be.
Substitution vs. Elimination: Reagent

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Determine the function of the reagent: assess the strength of a base:
! Quantitatively, using the pK
a
of its conjugate acid
! Qualitatively, using ARIO (atom, resonance, induction, orbital)
Classication of Common Reagents Used for Substition/Elimination
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strong
conjugate acids)
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strong
conjugate acids)
Very low polarizability,
sterically hindered
23
Classication of Common Reagents Used for Substition/Elimination Classication of Common Reagents Used for Substition/Elimination
DBN
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strong
conjugate acids)
Very low polarizability,
sterically hindered
Stronger reagents,
promote S
N
2 or E2
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strong
conjugate acids)
Very low polarizability,
sterically hindered
Stronger reagents,
promote S
N
2 or E2
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strong
conjugate acids)
Very low polarizability,
sterically hindered
Stronger reagents,
promote S
N
2 or E2
Weaker reagents,
promote S
N
1 or E1
Substitution vs. Elimination#

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
24
Identifying the Mechanism(s): 1. Reagent and 2. Substrate Identifying the Mechanism(s): 1. Reagents: Nucleophiles (only)
Identifying the Mechanism(s): 1. Reagents: Nucleophiles (only) Identifying the Mechanism(s): 1. Reagents: Nucleophiles (only)
Identifying the Mechanism(s): 1. Reagents: Nucleophiles (only)
"The rate enhance-
ment by using polar
aprotic solvent

Identifying the Mechanism(s): 1. Reagents: Bases (only)
"E2 mechanism is not
sensitive to steric hindrance.
25
Identifying the Mechanism(s): 1. Reagents: Bases (only)
"E2 mechanism is not
sensitive to steric hindrance.
1. Reagents: Strong Nucleophile and Strong Bases Competition
"E2 mechanism is not
sensitive to steric hindrance.
1. Reagents: Strong Nucleophile and Strong Bases Competition 1. Reagents: Strong Nucleophile and Strong Bases Competition
1. Reagents: Strong Nucleophile and Strong Bases Competition 1. Reagents: Strong Nucleophile and Strong Bases Competition
26
1. Reagents: Strong Nucleophile and Strong Bases Competition 1. Reagents: Strong Nucleophile and Strong Bases Competition
1. Reagents: Strong Nucleophile and Strong Bases Competition 1. Reagents: Weak Nucleophile and Strong Bases Competition
The reaction is too
slow!
1. Reagents: Weak Nucleophile and Strong Bases Competition
The reaction is too
slow, and too many
product are formed!
1. Reagents: Weak Nucleophile and Strong Bases Competition
27
1. Reagents: Weak Nucleophile and Strong Bases Competition
at high temperature, E1
Well..
Not to just memorize, but understand/digest
Substitution vs. Elimination#

To predict whether substitution or elimination will predominate, consider the
factors below:

1. Determine the function of the reagent. Is it more likely to act as a
base, a nucleophile, or both?
a. Kinetics control nucleophilicity. (the rate, good at reacting)
b. Thermodynamics control basicity. (the position of equilibrium)

2. Analyze the substrate and predict the expected mechanism (S
N
1,
S
N
2, E1, or E2).

3. Consider relevant regiochemical and stereochemical requirements.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
S
n
2 1he nucleophlle auacks Lhe o
posluon, where Lhe leavlng
group ls connecLed.
1he nucleophlle replaces Lhe
leavlng group wlLh lnverslon of
congurauon.
S
n
1 1he nucleophlle auacks Lhe
carbocauon, whlch ls where Lhe
leavlng group was orlglnally
connecLed, unless a carbocauon
rearrangemenL Look place.
1he nucleophlle replaces Lhe
leavlng group wlLh racemlzauon.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
S
n
2 1he nucleophlle auacks Lhe o
posluon, where Lhe leavlng
group ls connecLed.
1he nucleophlle replaces Lhe
leavlng group wlLh lnverslon of
congurauon.
S
n
1 1he nucleophlle auacks Lhe
carbocauon, whlch ls where Lhe
leavlng group was orlglnally
connecLed, unless a carbocauon
rearrangemenL Look place.
1he nucleophlle replaces Lhe
leavlng group wlLh racemlzauon.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
L2 1he ZalLsev producL ls generally
favored over Lhe Pofmann producL,
unless a sLerlcally hlndered base ls
used, ln whlch case Lhe Pofmann
producL wlll be favored
1hls process ls boLh sLereoselecuve
and sLereospeclc.
When appllcable, a !"#$% dlsubsuLuLed
alkene wlll be favored over a &'%
dlsubsuLuLed alkene. When Lhe
posluon of Lhe subsLraLe has only one
proLon, Lhe sLereolsomerlc alkene
resulung from anu-perlplanar
ellmlnauon wlll be obLalned
(excluslvely, ln mosL cases).
L1 1he ZalLsev producL ls always
favored over Lhe Pofmann producL.
1he process ls sLereoselecuve. When
appllcable, a !"#$% dlsubsuLuLed alkene
wlll be favored over a &'% dlsubsuLuLed
alkene.
28
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
L2 1he ZalLsev producL ls generally
favored over Lhe Pofmann producL,
unless a sLerlcally hlndered base ls
used, ln whlch case Lhe Pofmann
producL wlll be favored
1hls process ls boLh sLereoselecuve
and sLereospeclc.
When appllcable, a !"#$% dlsubsuLuLed
alkene wlll be favored over a &'%
dlsubsuLuLed alkene. When Lhe
posluon of Lhe subsLraLe has only one
proLon, Lhe sLereolsomerlc alkene
resulung from anu-perlplanar
ellmlnauon wlll be obLalned
(excluslvely, ln mosL cases).
L1 1he ZalLsev producL ls always
favored over Lhe Pofmann producL.
1he process ls sLereoselecuve. When
appllcable, a !"#$% dlsubsuLuLed alkene
wlll be favored over a &'% dlsubsuLuLed
alkene.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
L2 1he ZalLsev producL ls generally
favored over Lhe Pofmann producL,
unless a sLerlcally hlndered base ls
used, ln whlch case Lhe Pofmann
producL wlll be favored
1hls process ls boLh sLereoselecuve
and sLereospeclc.
When appllcable, a !"#$% dlsubsuLuLed
alkene wlll be favored over a &'%
dlsubsuLuLed alkene. When Lhe
posluon of Lhe subsLraLe has only one
proLon, Lhe sLereolsomerlc alkene
resulung from anu-perlplanar
ellmlnauon wlll be obLalned
(excluslvely, ln mosL cases).
L1 1he ZalLsev producL ls always
favored over Lhe Pofmann producL.
1he process ls sLereoselecuve. When
appllcable, a !"#$% dlsubsuLuLed alkene
wlll be favored over a &'% dlsubsuLuLed
alkene.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
L2 1he ZalLsev producL ls generally
favored over Lhe Pofmann producL,
unless a sLerlcally hlndered base ls
used, ln whlch case Lhe Pofmann
producL wlll be favored
1hls process ls boLh sLereoselecuve
and sLereospeclc.
When appllcable, a !"#$% dlsubsuLuLed
alkene wlll be favored over a &'%
dlsubsuLuLed alkene. When Lhe
posluon of Lhe subsLraLe has only one
proLon, Lhe sLereolsomerlc alkene
resulung from anu-perlplanar
ellmlnauon wlll be obLalned
(excluslvely, ln mosL cases).
L1 1he ZalLsev producL ls always
favored over Lhe Pofmann producL.
1he process ls sLereoselecuve. When
appllcable, a !"#$% dlsubsuLuLed alkene
wlll be favored over a &'% dlsubsuLuLed
alkene.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
8LClCCPLMlCAL Cu1CCML S1L8LCCPLMlCAL Cu1CCML
L2 1he ZalLsev producL ls generally
favored over Lhe Pofmann producL,
unless a sLerlcally hlndered base ls
used, ln whlch case Lhe Pofmann
producL wlll be favored
1hls process ls boLh sLereoselecuve
and sLereospeclc.
When appllcable, a !"#$% dlsubsuLuLed
alkene wlll be favored over a &'%
dlsubsuLuLed alkene. When Lhe
posluon of Lhe subsLraLe has only one
proLon, Lhe sLereolsomerlc alkene
resulung from anu-perlplanar
ellmlnauon wlll be obLalned
(excluslvely, ln mosL cases).
L1 1he ZalLsev producL ls always
favored over Lhe Pofmann producL.
1he process ls sLereoselecuve. When
appllcable, a !"#$% dlsubsuLuLed alkene
wlll be favored over a &'% dlsubsuLuLed
alkene.
Lets Solve this Problem Together! Lets Solve this Problem Together!
29
Lets Solve this Problem Together! Lets Solve this Problem Together!
Lets Solve this Problem Together! Lets Solve this Problem Together!