Summary of 5 mechanism

Free Radical Subsitution (Alkane) Electrophilic Substitution (Arene)

Step 1: initiation Step 1:
uv HNO3 + 2 H2SO4 U NO2+ + 2 HSO4- + H3O+
Cl Cl Cl + Cl
Step 2:
Step 2: Propagation H NO2
Cl H CH2CH3 CH3CH2• HCl
CH3CH2• Cl Cl CH3CH2 Cl Cl + slow
NO2 +
Step 3: Termination
CH3CH2• Cl CH3CH2 Cl
Step 3:
NO2
Cl Cl Cl Cl H NO2
fast
CH3CH2• CH3CH2• CH3CH2 CH2CH3 .. - + + H2SO4
HSO4

Electrophilic Addition (Alkene)

Step 1: Polarisation of Br−Br bond by p electron cloud of ethene Step 1:
H H
C Cl2 + AlCl3 U Cl+ + AlCl4-
δ+ δ−
Br Br Step 2:
C
H Cl
H H
Step 2: + slow
Cl +
H
H H
C δ+ δ− slow H C+
Br Br + Br- Step 3:
C H C Br Cl
H Cl
H H H
Step 3: .. - fast + AlCl3 + HCl
+
H AlCl4
H
+
H C - fast H C Br
+ Br
H C Br H C Br
H H

Prepared by NYJC Science Department / Chemistry 2011 1

 Summary of 5 mechanism
Nucleophilic Substitution (Halogenoalkane) Nucleophilic Addition (Carbonyl)
SN2 Mechanism Step 1:
_
_ HCN + NaOH Na+ + CN + H2O
H H H
− δ+ δ-
HO C Br HO C
-
Br HO C + Br
− Step 2:
H H
CH3 CH3 H CH3 CH3
H3C
δ+ δ- _
NC __ C
H H H C O slow
O
δ+ δ- .. _
-
+ CN H3C
.. 0
NH 3 C Br H 3N C Br H2 N C HBr
H H CH3
CH 3 CH 3 H CH 3

Step 3:
SN1 Mechanism CH3 CH3
Step 1 :
CH3 CH3 .. _ _
NC __ C O + H
_
CN
fast
NC __ C OH + CN
δ+ δ− slow
H3C C Br H3C C+ + Br
−
CH3 CH3

CH3 CH3
Step 2: Things to note for mechanism questions:
CH3 CH3
1) State name of mechanism
− fast
H3C C+ OH H3C C OH
2) Indicate fast/slow step (if applicable)
3) Be careful to show clearly and correctly the following:
a. direction of arrow (be clear where it should start and end)
CH3 CH3 b. lone pair of electrons
c. δ+, δ-
*Note that above are meant for reference, please read question
carefully and draw the correct compounds when answering!

Prepared by NYJC Science Department / Chemistry 2011 2