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Amit Z Chaudhari
C O N T E N T
2
- Structure
- Stability
- Preparation
- Reactions
- Dials Alder reaction
- electrophilic addition reaction
- Free-radical addition reaction
C L A S S I F I C A T I O N
hydrocarbons having two carbon–carbon double bond
Synonym: Alkadienes
Gen. formula: CnH2n-2
- Nomenclature similarity with alkene, For a compound with two
double bonds, the “ne” ending of the corresponding alkane is replaced
with “diene.”
- General formula similarity with alkynes , thus isomeric with alkynes
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 3
C L A S S I F I C A T I O N
Structure :
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 4
S t a b i l i t y
- Heat of hydrogenation reveals the relative stability of dienes
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 5
S t a b i l i t y
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 6
Stability is due to Resonance in conjugated dienes :
S t a b i l i t y
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 7
Stability is due to Resonance in conjugated dienes :
S t a b i l i t y
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
Delocalized π electrons
Orbital structure of 1,3-Butadiene
8
Q.
GPAT
For 1,3-butadiene, there are ___ molecular orbitals for p electrons.
2021 A. 2 C. 4
B. 6 D. 8
P r e p a r a t i o n
※ Bahl & Bahl ※ Mehta & Mehta ※ Francis A. Carey ※ Paula Bruice ※ 9
※ Bahl & Bahl ※ Mehta & Mehta ※ Francis A. Carey ※ Paula Bruice ※
P r e p a r a t i o n
10
R e a c t i o n s
Diel-Alder reaction
Electrophilic addition,
Free radical addition
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 11
D i e l s – A l d e r r e a c t i o n
Cycloaddition: an addition reaction in which a cyclic molecule is
formed.
e.g. Diels–Alder reaction
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
S-cis prefers dies alder reaction
12
[4+2] Cycloaddition reaction : because four of the six p electrons that
participate in the cyclic transition state come from the conjugated diene and
two come from the dienophile.
Concerted reaction
Mechanism
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
1,4-addition reaction : sp2 C of dienophile adds to 1,4 C of diene
13
D i e l s – A l d e r r e a c t i o n
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
The reactivity of the dienophile is increased if an electron-withdrawing
group is attached to one of its sp2 carbons.
14
D i e l s – A l d e r r e a c t i o n
transition states in Diels–Alder reaction
(1) Syn-addition
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 15
D i e l s – A l d e r r e a c t i o n
(2) Stereo specific reaction
※ Paula Bruice ※ 16
D i e l s – A l d e r r e a c t i o n
17
Q.
NIPE
R
Which of the following diene is most reactive in Diels-Alder reaction?
2018 A. C.
B. D.
S-cis prefers dies alder reaction
D i e l s – A l d e r r e a c t i o n
E l e c t r o p h i l i c A d d i t i o n
electrophilic addition to nonconjugated diene :
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 18
electrophilic addition to conjugated diene :
E l e c t r o p h i l i c A d d i t i o n
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 19
electrophilic addition to conjugated diene :
Mechanism
Compare the stability of both possible
intermediates
E l e c t r o p h i l i c A d d i t i o n
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
Allylic cation
20
E l e c t r o p h i l i c A d d i t i o n
Step_1: addition of electrophile to = bonded C. Formation of carbocation
- Addition may occur in to C2 or C3 atoms.
- Both condition create 2oC+ , but intermediate II is ally cation ,
formed predominantly because of resonance stabilization (of allyl
cation).
Step_2: attack of Cl- to C+
- As in contributing structure C3 and C5 both have equal distribution of
+ve charge , equal chance of pathway 1 and pathway 2
- Attack of Cl- at C3 gives 1,2- and attack at C5 gives 1,4-addition pdct.
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 21
1 , 2 - v s 1 , 4 - a d d i t i o n
1,2- vs 1,4- addition /
rate vs equilibrium /
40oC 20% 80%
- 80oC 80% 20%
kinetic & thermodynamically controlled rxn
22
※ Morrison & Boyd ※
1,2- vs 1,4- addition: reversible rxn btwn 1,2- & 1,4-
23
※ Morrison & Boyd ※
1 , 2 - v s 1 , 4 - a d d i t i o n
1,2- vs 1,4- addition: potential energy diagram
24
※ Morrison & Boyd ※
1 , 2 - v s 1 , 4 - a d d i t i o n
i.e. 1,2- addition pdct predominates at low temp.
i.e. 1,4- addition pdct predominates at High temp.
25
※ Morrison & Boyd ※
1 , 2 - v s 1 , 4 - a d d i t i o n
F r e e - r a d i c a l a d d i t i o n
Free-radical addition to conjugated dienes :
Example:
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 26
F r e e - r a d i c a l a d d i t i o n
Mechanism:
Step 1 chain initiation
- C-Cl bond is stronger than C-Br bond thus phenyl radical abstract
bromine from BrCCl3, not chlorine
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 27
F r e e - r a d i c a l a d d i t i o n
Mechanism:
Step 2 formation of allyl radical
※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※
Step 3 formation of 1,2- and 1,4- pdct
Allylic free radical
28
Reference:
Organic Chemistry - Morrison, Boyd
Organic chemistry- Mehta & Mehta
Organic Chemistry - Paula Bruice

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DIENES _ Organic Chemistry _ B. Pharm..pptx

  • 2. C O N T E N T 2 - Structure - Stability - Preparation - Reactions - Dials Alder reaction - electrophilic addition reaction - Free-radical addition reaction
  • 3. C L A S S I F I C A T I O N hydrocarbons having two carbon–carbon double bond Synonym: Alkadienes Gen. formula: CnH2n-2 - Nomenclature similarity with alkene, For a compound with two double bonds, the “ne” ending of the corresponding alkane is replaced with “diene.” - General formula similarity with alkynes , thus isomeric with alkynes ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 3
  • 4. C L A S S I F I C A T I O N Structure : ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 4
  • 5. S t a b i l i t y - Heat of hydrogenation reveals the relative stability of dienes ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 5
  • 6. S t a b i l i t y ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 6
  • 7. Stability is due to Resonance in conjugated dienes : S t a b i l i t y ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 7
  • 8. Stability is due to Resonance in conjugated dienes : S t a b i l i t y ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ Delocalized π electrons Orbital structure of 1,3-Butadiene 8 Q. GPAT For 1,3-butadiene, there are ___ molecular orbitals for p electrons. 2021 A. 2 C. 4 B. 6 D. 8
  • 9. P r e p a r a t i o n ※ Bahl & Bahl ※ Mehta & Mehta ※ Francis A. Carey ※ Paula Bruice ※ 9
  • 10. ※ Bahl & Bahl ※ Mehta & Mehta ※ Francis A. Carey ※ Paula Bruice ※ P r e p a r a t i o n 10
  • 11. R e a c t i o n s Diel-Alder reaction Electrophilic addition, Free radical addition ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 11
  • 12. D i e l s – A l d e r r e a c t i o n Cycloaddition: an addition reaction in which a cyclic molecule is formed. e.g. Diels–Alder reaction ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ S-cis prefers dies alder reaction 12
  • 13. [4+2] Cycloaddition reaction : because four of the six p electrons that participate in the cyclic transition state come from the conjugated diene and two come from the dienophile. Concerted reaction Mechanism ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 1,4-addition reaction : sp2 C of dienophile adds to 1,4 C of diene 13 D i e l s – A l d e r r e a c t i o n
  • 14. ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ The reactivity of the dienophile is increased if an electron-withdrawing group is attached to one of its sp2 carbons. 14 D i e l s – A l d e r r e a c t i o n
  • 15. transition states in Diels–Alder reaction (1) Syn-addition ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 15 D i e l s – A l d e r r e a c t i o n
  • 16. (2) Stereo specific reaction ※ Paula Bruice ※ 16 D i e l s – A l d e r r e a c t i o n
  • 17. 17 Q. NIPE R Which of the following diene is most reactive in Diels-Alder reaction? 2018 A. C. B. D. S-cis prefers dies alder reaction D i e l s – A l d e r r e a c t i o n
  • 18. E l e c t r o p h i l i c A d d i t i o n electrophilic addition to nonconjugated diene : ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 18
  • 19. electrophilic addition to conjugated diene : E l e c t r o p h i l i c A d d i t i o n ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 19
  • 20. electrophilic addition to conjugated diene : Mechanism Compare the stability of both possible intermediates E l e c t r o p h i l i c A d d i t i o n ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ Allylic cation 20
  • 21. E l e c t r o p h i l i c A d d i t i o n Step_1: addition of electrophile to = bonded C. Formation of carbocation - Addition may occur in to C2 or C3 atoms. - Both condition create 2oC+ , but intermediate II is ally cation , formed predominantly because of resonance stabilization (of allyl cation). Step_2: attack of Cl- to C+ - As in contributing structure C3 and C5 both have equal distribution of +ve charge , equal chance of pathway 1 and pathway 2 - Attack of Cl- at C3 gives 1,2- and attack at C5 gives 1,4-addition pdct. ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 21
  • 22. 1 , 2 - v s 1 , 4 - a d d i t i o n 1,2- vs 1,4- addition / rate vs equilibrium / 40oC 20% 80% - 80oC 80% 20% kinetic & thermodynamically controlled rxn 22 ※ Morrison & Boyd ※
  • 23. 1,2- vs 1,4- addition: reversible rxn btwn 1,2- & 1,4- 23 ※ Morrison & Boyd ※ 1 , 2 - v s 1 , 4 - a d d i t i o n
  • 24. 1,2- vs 1,4- addition: potential energy diagram 24 ※ Morrison & Boyd ※ 1 , 2 - v s 1 , 4 - a d d i t i o n
  • 25. i.e. 1,2- addition pdct predominates at low temp. i.e. 1,4- addition pdct predominates at High temp. 25 ※ Morrison & Boyd ※ 1 , 2 - v s 1 , 4 - a d d i t i o n
  • 26. F r e e - r a d i c a l a d d i t i o n Free-radical addition to conjugated dienes : Example: ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 26
  • 27. F r e e - r a d i c a l a d d i t i o n Mechanism: Step 1 chain initiation - C-Cl bond is stronger than C-Br bond thus phenyl radical abstract bromine from BrCCl3, not chlorine ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ 27
  • 28. F r e e - r a d i c a l a d d i t i o n Mechanism: Step 2 formation of allyl radical ※ Morrison & Boyd ※ Mehta & Mehta ※ Paula Bruice ※ Step 3 formation of 1,2- and 1,4- pdct Allylic free radical 28
  • 29. Reference: Organic Chemistry - Morrison, Boyd Organic chemistry- Mehta & Mehta Organic Chemistry - Paula Bruice

Editor's Notes

  1. Cuprous chloride and ammonium chloride
  2. Adsorption: homolytic cleavage of hydrogen molecules 2. Hydrogen atoms becomes attached to a carbon atom, creating in effect, an alkyl radical 3. Transfer of a hydrogen atom to carbon opens a site on the metal catalyst for coordination to additional hydrogen atoms.