Mechanisms in Organic Chemistry Alkenes Aldehydes or ketones Halogenoalka nes Arenes Alkanes Electroph ilic Addition HBr , Br 2 ,Br 2(aq) Free Radical Polymer isation Nucleophi lic Addition Nucleophilic Substitutio n S N 1 S N 2 Electrophi lic Substitut ion Free Radi cal Subst itution
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Mechanisms in Organic Chemistry AlkenesAldehydes or ketones HalogenoalkanesArenesAlkanes Electrophilic Addition HBrHBr, Br 2, Br 2(aq)Br 2 Br 2(aq) Free.
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Mechanisms in Organic Chemistry
Alkenes Aldehydes or ketones
Halogenoalkanes Arenes Alkanes
Electrophilic
AdditionHBr, Br2,Br2(aq)
Free Radical
Polymerisation
Nucleophilic Addition
Nucleophilic Substitution
SN1
SN2
Electrophilic Substitution
Free Radical Substitution
Electrophilic Addition 1 – Ethene + HBr
H
Br _
+
CC
H
H
H
H H+
:Br_
CC
H
Br H
H
H HC C
H
H H
H
home
Electrophilic Addition 2 – Ethene + Br2(hexane)
Br
Br _
+
CC
H
Br
H
H H+
:Br_
CC
H
Br Br
H
H HC C
H
H H
H
home
Electrophilic Addition 3 – Ethene + Br2(aq)
Br
Br _
+
CC
H
Br
H
H H+
:OH2
CC
H
OH Br
H
H HC 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_
+
_
home
C CH3
CH3
H3C
OH
C CH3
CH3
H3C
Br
C CH3
CH3
H3C +
:Br-
+
- :OH-
Nucleophilic Substitution – SN1 Mechanism
Rate = k[C4H9Br]home
CC
H
H H
H
H Br CC
H
H H
H
H OH
:OH-
Nucleophilic Substitution – SN2 Mechanism
Rate = k[C2H5Br][:OH-]
:Br-
home
+ _
(NB Transition state)
Electrophilic Substitution 1 – Nitration of benzene
H2SO4 + HNO3 NO2+ + HSO4
- + H2O
home
+
NO2H+NO2NO2
H+
Electrophilic Substitution 2 – Bromination of benzene
Br2 + AlCl3 Br+ + AlBrCl3-
home
+
BrH+Br Br
HBr
AlCl3
Electrophilic Substitution 3 – Alkylation of benzene
CH3Cl + AlCl3 CH3+ + AlCl4
-
home
+
CH3H+CH3CH3
HCl
AlCl3
Electrophilic Substitution 4 – Acylation of benzene