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Mechanisms in Organic
Chemistry
Alkenes Aldehydes
or ketones
Halogenoalkanes Arenes Alkanes
Electrophilic
Addition
HBr, Br2,Br2(aq)
Free Radical
Polymerisation
Nucleophilic
Addition
Nucleophilic
Substitution
SN1
SN2
Electrophilic
Substitution
Free Radical
Substitution
Electrophilic Addition 1 – Ethene + HBr
H
Br
d
_
d+
C
C
H
H
H
H H
+
:Br
_
C
C
H
Br H
H
H H
C C
H
H H
H
home
Electrophilic Addition 2 – Ethene + Br2(hexane)
Br
Br
d
_
d+
C
C
H
Br
H
H H
+
:Br
_
C
C
H
Br Br
H
H H
C C
H
H H
H
home
Electrophilic Addition 3 – Ethene + Br2(aq)
Br
Br
d
_
d+
C
C
H
Br
H
H H
+
:OH2
C
C
H
OH Br
H
H H
C C
H
H H
H
home
:Br
_
HBr
Nucleophilic Addition – Reaction of HCN with Carbonyls
C
O
H3C H
C
:O
_
H3C H
CN
C
:OH
H3C H
CN
H+
:CN
_
d+
d
_
home
C CH3
CH3
H3C
OH
C CH3
CH3
H3C
Br
C CH3
CH3
H3C
+
:Br-
d+
d- :OH-
Nucleophilic Substitution – SN1 Mechanism
Rate = k[C4H9Br]
home
C
C
H
H H
H
H Br C
C
H
H H
H
H OH
:OH-
Nucleophilic Substitution – SN2 Mechanism
Rate = k[C2H5Br][:OH-]
:Br-
home
d+ d
_
(NB Transition state)
Electrophilic Substitution 1 – Nitration of benzene
H2SO4 + HNO3 NO2
+ + HSO4
- + H2O
home
+
NO2
H
+NO2
NO2
H+
Electrophilic Substitution 2 – Bromination of benzene
Br2 + AlCl3 Br+ + AlBrCl3
-
home
+
Br
H
+Br Br
HBr
AlCl3
Electrophilic Substitution 3 – Alkylation of benzene
CH3Cl + AlCl3 CH3
+ + AlCl4
-
home
+
CH3
H
+CH3
CH3
HCl
AlCl3
Electrophilic Substitution 4 – Acylation of benzene
CH3COCl + AlCl3 CH3CO+ + AlCl4
-
home
+
CH3
C
O
H
CH3
+C
O
CH3
C
O
HCl
AlCl3
Br+
Bromination of methylbenzene – ring substitution
AlBr3
HBr
Br2 + AlBr3 Br+ + AlBr4
-
CH3
Br
home
CH3 CH3
+
H
Br
Free Radical Substitution 1 – Methane + Cl2
Initiation Cl Cl
u.v. light
2Cl
.
Propagation CH4 + Cl
. . CH3 + HCl
. CH3 + Cl2 CH3Cl + Cl
.
Termination . CH3 +
. CH3
C2H6
. CH3 +
. Cl CH3Cl
home
Free Radical Addition Polymerisation of Ethene
home
R
C C
H
H H
H
C C
H
H H
H
C
C
H
H H
H
R
C
C
H
H H
H
R
C
C
H
H H
H
R C
C
H
H H
H
Propagation
Initiation
R R
heat
2R
.

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qorg - sldie mechanisms in organic chemistry.ppt

  • 1. Mechanisms in Organic Chemistry Alkenes Aldehydes or ketones Halogenoalkanes Arenes Alkanes Electrophilic Addition HBr, Br2,Br2(aq) Free Radical Polymerisation Nucleophilic Addition Nucleophilic Substitution SN1 SN2 Electrophilic Substitution Free Radical Substitution
  • 2. Electrophilic Addition 1 – Ethene + HBr H Br d _ d+ C C H H H H H + :Br _ C C H Br H H H H C C H H H H home
  • 3. Electrophilic Addition 2 – Ethene + Br2(hexane) Br Br d _ d+ C C H Br H H H + :Br _ C C H Br Br H H H C C H H H H home
  • 4. Electrophilic Addition 3 – Ethene + Br2(aq) Br Br d _ d+ C C H Br H H H + :OH2 C C H OH Br H H H C C H H H H home :Br _ HBr
  • 5. Nucleophilic Addition – Reaction of HCN with Carbonyls C O H3C H C :O _ H3C H CN C :OH H3C H CN H+ :CN _ d+ d _ home
  • 6. C CH3 CH3 H3C OH C CH3 CH3 H3C Br C CH3 CH3 H3C + :Br- d+ d- :OH- Nucleophilic Substitution – SN1 Mechanism Rate = k[C4H9Br] home
  • 7. C C H H H H H Br C C H H H H H OH :OH- Nucleophilic Substitution – SN2 Mechanism Rate = k[C2H5Br][:OH-] :Br- home d+ d _ (NB Transition state)
  • 8. Electrophilic Substitution 1 – Nitration of benzene H2SO4 + HNO3 NO2 + + HSO4 - + H2O home + NO2 H +NO2 NO2 H+
  • 9. Electrophilic Substitution 2 – Bromination of benzene Br2 + AlCl3 Br+ + AlBrCl3 - home + Br H +Br Br HBr AlCl3
  • 10. Electrophilic Substitution 3 – Alkylation of benzene CH3Cl + AlCl3 CH3 + + AlCl4 - home + CH3 H +CH3 CH3 HCl AlCl3
  • 11. Electrophilic Substitution 4 – Acylation of benzene CH3COCl + AlCl3 CH3CO+ + AlCl4 - home + CH3 C O H CH3 +C O CH3 C O HCl AlCl3
  • 12. Br+ Bromination of methylbenzene – ring substitution AlBr3 HBr Br2 + AlBr3 Br+ + AlBr4 - CH3 Br home CH3 CH3 + H Br
  • 13. Free Radical Substitution 1 – Methane + Cl2 Initiation Cl Cl u.v. light 2Cl . Propagation CH4 + Cl . . CH3 + HCl . CH3 + Cl2 CH3Cl + Cl . Termination . CH3 + . CH3 C2H6 . CH3 + . Cl CH3Cl home
  • 14. Free Radical Addition Polymerisation of Ethene home R C C H H H H C C H H H H C C H H H H R C C H H H H R C C H H H H R C C H H H H Propagation Initiation R R heat 2R .