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for example:
O
H3O
BH
H
H2O
for example:
CH3
H3C
Cl
CH3
H2O
CH3
H3C
C
CH3
Cl
Nu
Nu
or:
Nu
E
C
+ E
R
C
Nu
Nu
Nu
+ X
Nu
Nu
Nu
Nu
+ X
Note that substitution reactions of this kind may occur at heteroatom centres
as well as at carbon.
BH
C
X
B
C
C
X
C
X
BH
H
C
C
X
X
BH
BH
C
X
C
X
HB
C
HB
H
C
H
C
HB
HB
H
C
Note that this pathway can also involve heteroatom centres (e.g. carbonyls)
and Lewis acids.
Polarized multiple bonds include carbonyls, imines etc. and also alkenes
substituted by electron withdrawing groups. All the variations in charge shown
for previous reactions apply here as well, but are omitted for simplicity.
Nu
Nu
Nu
C
or:
EWG
C
EWG
11. -Elimination from an anion or a lone pair (DN; reverse of process 10)
X
X
C
OH
OH
OCH3
OCH3
HO
HO
HOH
OH
or:
Cl
Cl
H 2O
O
O
H
Cl
H
Cl
CH3
CH3
H3C
H3C
H3C
CH3
CH3
H3C
H3C
CH3
H3C
CH3
Cl
H
Cl
Cl
H
H O
H
CH3
O
+ HOCH3
H
H
Br
Br
O
C
2. 1,2 Rearrangement to an electron deficient center with loss of Nu, a special case
of the 1,2R pathway
O
HO
O
R
O
1
R +
OR2
OH2
N
C
O
+ H2O
Br
O + Br
Ph
P
Ph
+ Ph
P
Ph