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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
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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 bondthe lowest number possible.
4. Assemble the name alphabetically.
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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 bondthe 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
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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).
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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
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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
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E2: Kinetics
E2: A concerted mechanism
The kinetics of E2 and S N2 are quite similar!
E2
E2: A concerted mechanism
E2: Effect of Substrate
Tertiary substrates are unreactive toward
S N2 while they react readily by E2.
E2: Effect of Substrate
! ! !
E2: Effect of Substrate E2: Energy Diagram
Look at TS-->
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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
H3C H3C
H
H H
H3C (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
H3C
H3C
H
H H
H3C (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
H3C
H3C
H
H H
H3C (1) (2)
(3)
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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
H3C
H3C
H
H H
H3C (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.
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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 ofthe orbitals in the transition state for the reaction.
! In the transition state, the CH and CBr bonds that are breaking must berotated into the same plane as the pi bond that is forming.
E2: Stereospecicity
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E2: Stereospecicity E2: Stereospecicity
E2: Stereospecicity
! Evidence suggests that a strict 180 angle is not necessary for E2mechanisms.
! 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 congurationof the starting alkyl halide.
E2: Stereospecicity
! Evidence suggests that a strict 180 angle is not necessary for E2mechanisms.
! 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 congurationof the starting alkyl halide.
E2: Stereospecicity Anti -Periplanar E2: Stereospecicity Anti -Periplanar
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Cl
Base
+ HBase2.
The rate of E2 reaction is greatly affected by theamount of time that the leaving group spends inan axial position. Which is more reactive?
3.
Me Me Me
ClMe ClMe
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar
+
Cl
Base
+ HBase2.
The rate of E2 reaction is greatly affected by theamount of time that the leaving group spends inan axial position. Which is more reactive?
3.
Me Me Me
ClMe ClMe
vs.
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar
+
The rate of E2 reaction is greatly affected by theamount of time that the leaving group spends inan axial position. Which is more reactive?
3.
ClMe ClMe
vs.
Neomenthyl chloride Menthyl chloride
E2: Stereospecicity on Substituted Cyclohexanes (Take-Home Quiz)
Anti-Periplanar
The rate of E2 reaction is greatly affected by theamount of time that the leaving group spends inan axial position. Which is more reactive?
3.
ClMe ClMe
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 theamount of time that the leaving group spends inan axial position. Which is more reactive?
3.
ClMe ClMe
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
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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
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E1 E1
E1 E1
E1: 1. Effect of Substrate Similar with S N1 E1: 1. Effect of Substrate
Because E1 and S N1 proceed by the same rst step, their competition willgenerally result in a mixture of products
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E1: 1. Effect of Substrate
Because E1 and S N1 proceed by the same rst step, their competition willgenerally 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 N1 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
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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 orelimination.
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 orelimination.
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 orelimination.
Sometimes a mixture of products is observed.
8.12 Substitution vs. Elimination #
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent #
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent #
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
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Substitution vs. Elimination: Reagent #
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, 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 thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
Substitution vs. Elimination: Reagent
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, 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 p K 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 strongconjugate acids)
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strongconjugate acids)
Very low polarizability,sterically hindered
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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 strongconjugate acids)
Very low polarizability,sterically hindered
Stron ger reagents,
promote S N2 or E2
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strongconjugate acids)
Very low polarizability,sterically hindered
Stron ger reagents,
promote S N2 or E2
Classication of Common Reagents Used for Substition/Elimination
Highly polarizable,
weak bases (very strongconjugate acids)
Very low polarizability,sterically hindered
Stronger reagents,
promote S N2 or E2
Weaker reagents,
promote S N1 or E1
Substitution vs. Elimination #
To predict whether substitution or elimination will predominate, consider thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
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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 polaraprotic solvent
Identifying the Mechanism(s): 1. Reagents: Bases (only)
" E2 mechanism is notsensitive to steric hindrance.
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Identifying the Mechanism(s): 1. Reagents: Bases (only)
" E2 mechanism is notsensitive to steric hindrance.
1. Reagents: Strong Nucleophile and Strong Bases Competition
" E2 mechanism is notsensitive 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
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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 thefactors below:
1. Determine the function of the reagent. Is it more likely to act as abase, 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 N1,S N2, E1, or E2).
3. Consider relevant regiochemical and stereochemical requirements.
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
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Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
!"#$%&'"($&)* %,-&%(" .-"!"%&'"($&)* %,-&%("
. / 0 -12 34562781962 :;:512 ?87=9@73A B12C2 >12 62:D93EEC748 9= 573325>2FG
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. / J -12 34562781962 :;:512
5:CK75:@73A B1951 9= B12C2 >1262:D93E EC748 B:= 7C9E93:66L573325>2FA 4362== : 5:CK75:@73C2:CC:3E2M23> >77< 86:52G
-12 34562781962 C286:52= >12
62:D93E EC748 B9>1 C:52M9N:@73G
Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
!"#$%&'"($&)* %,-&%(" .-"!"%&'"($&)* %,-&%("
"0 -12 O:9>=2D 8C7F45> 9= E232C:66LH:D7C2F 7D2C >12 '7HM:33 8C7F45>A4362== : =>2C95:66L 193F2C2F K:=2 9=4=2FA 93 B1951 5:=2 >12 '7HM:338C7F45> B966 K2 H:D7C2F
-19= 8C752== 9= K7>1 =>2C27=2625@D2:3F =>2C27=8259I5GP123 :88695:K62A : !"#$% F9=4K=@>4>2F:6G
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Regio- and Stereochemical Outcome of Substitution and Elimination Reactions
!"#$%&'"($&)* %,-&%(" .-"!"%&'"($&)* %,-&%("
"0 -12 O:9>=2D 8C7F45> 9= E232C:66LH:D7C2F 7D2C >12 '7HM:33 8C7F45>A4362== : =>2C95:66L 193F2C2F K:=2 9=
4=2FA 93 B1951 5:=2 >12 '7HM:338C7F45> B966 K2 H:D7C2F
-19= 8C752== 9= K7>1 =>2C27=2625@D2:3F =>2C27=8259I5GP123 :88695:K62A : !"#$% F9=4K=@>4>2F
:6G
-12 8C752== 9= =>2C27=2625@D2G P123:88695:K62A : !"#$% F9=4K=@>4>2F :6A4362== : =>2C95:66L 193F2C2F K:=2 9=
4=2FA 93 B1951 5:=2 >12 '7HM:338C7F45> B966 K2 H:D7C2F
-19= 8C752== 9= K7>1 =>2C27=2625@D2:3F =>2C27=8259I5GP123 :88695:K62A : !"#$% F9=4K=@>4>2F
:6G
-12 8C752== 9= =>2C27=2625@D2G P123:88695:K62A : !"#$% F9=4K=@>4>2F :6A4362== : =>2C95:66L 193F2C2F K:=2 9=4=2FA 93 B1951 5:=2 >12 '7HM:338C7F45> B966 K2 H:D7C2F
-19= 8C752== 9= K7>1 =>2C27=2625@D2:3F =>2C27=8259I5GP123 :88695:K62A : !"#$% F9=4K=@>4>2F:6G
-12 8C752== 9= =>2C27=2625@D2G P123:88695:K62A : !"#$% F9=4K=@>4>2F :6A4362== : =>2C95:66L 193F2C2F K:=2 9=4=2FA 93 B1951 5:=2 >12 '7HM:338C7F45> B966 K2 H:D7C2F
-19= 8C752== 9= K7>1 =>2C27=2625@D2:3F =>2C27=8259I5GP123 :88695:K62A : !"#$% F9=4K=@>4>2F:6G
-12 8C752== 9= =>2C27=2625@D2G P123:88695:K62A : !"#$% F9=4K=@>4>2F :6
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Lets Solve this Problem Together! Lets Solve this Problem Together!
Lets Solve this Problem Together! Lets Solve this Problem Together!