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HYPERCONJUGATION
HYPERCONJUGATION
1
NO Bond Resonance
2 Baker nathaneffect
3 Co P conjugation
4
For
o plempty conjugation
For alkene
5
o
empty conjugation radical
for free
6
7
In Hyperconjugation consider sp a carbon of
following
a
ing
p
H H
9 THz 2 H
Enz 8h2
Enz
c
Chacha alkene Allylic H
dEnz Benzene Benzylic H
e THz CECH
Hyperconjugation in carbocation
gaz Ie
I Iq
No Bond
Hb ca
during
q
Hyperconj
dsp37x.c
N
so called
no Bond Reso
tis
Ifc's
of
delocalisation
called
iconjugation
C
é cha
r
Hb
hyper HE
is c
BR'D
Ig
going
going 1 o
ie TT
conjugation
the carbocation
of Hyperconj
involving C H bonds
Que
of following
TX 641h
6 Hyperconj Structure
Cuz CH CH3
I Tructures
3 K H
structures
BL H
g
GL H GL H
stability 1
2631
A A
77 B e
777 DJ
Ez
yet g
É Et
LI EE CE
C Hz Hz D C
Dz z th I
as C H CC D Bond
energy
so Extent of Hyperconjugation is C H C D
But
3 C ED no d
Hydrogen so no
Hyperconjugation only
Inductive eff
I D H
Ez 142
IE IE
2 142
t.EE eEi d
at meta
by Hyper
O
ÉÉ
Not 2
IF
a B
I 43
100
Eres
Es Es
143 245 I
to
2 CH3
sp3 x c with L H
millions mis
Ger
Hc
Sp3 C
with L H b CHz
Ya CHz
Hb C
HE
number c
Ed
D
I A B c
É a
yes sesame a
Y
Reso
A B C D E
B D A C
stability E
Bondevik
Bond a a D e B
energy
origin
NOTE R D H I
ne Ld
sp34 C
with 2 Hydrogen
Fa
fjÉÉÉ
Hb on E
O Tty
o empty I
Skytbphasemo
th
Ifan
it j
I
i
e
q
in
inphase MO
HE
ÉÉqA
Fbi
ch Iz
he
B o ca g Begg
B 0 1 2 B L did
B0 1 0 B L.TT
This is called o
empty conjugation
one
Bonds in
foitpmcongfat.ve
CI CE
I É É
2 cha ch ch
42 42 cuz ca cha
nd
64 H 62 H 62 H
BC
I I I
Ken 41143
cuz
by anion
Fanion 7 Zanion
Trans cis
so
D 4 6 stability
Que
943
y 64 H
Caz
43
P xylene m
xylene
And
HE 1 H H H
JaninOLI
EE cuz
I anion
3 anion Fanion
stability p xylene m
xylene
Cue
Compare stability
H h h
A B C
Out
compare the rate of Et attack
943 245
Y 1
y
E ET
A B C D
É
f E
yet
845
943 E Y
ITE
FEE ELE
32 H 24 H 14 H 02 H
stabilise
the Ave
charge
A B C D
Sacrificial Hyperconjugation If the contributing
formula
II
ÉÉ
n
I t In
to
go
2 F
II g
H cha H c cuz
I g
or ion
H
Elif H e ti I H
te g
p orbital to orbital
non
bonding É
or
N F overlap
f IF F É cha
Heat of combustion
of
2 for isomeric
AH combustion
stility
272 374
8
0
I II y
IT
A MI
3
D H
Y
gy
gy
following
energy profile diagram for Isomeric alkene
th
oncolb
Im
on
sp
Yo
aid in in an a man
column I column II 7
1 position isomers A P Q
2 Chain isomers B OT
3 G I C OR
one show G I E PS
Heat of Hydrogenation
DH
Hz PF Hydrogenation
stagey
X A A
stability 3 2
I 2 73
DHHyd
DHcomb I 7 2 73
II Hz 120 120 o
240 232
212
DHHyd ED
R E D
DHuyd per T
2080
12 23212 3
Exception
I I Id
Q compare DH
Hydrogenation
1 AL NV 1
ud ti 2am
EE EE
stability A B C D
DHHyd D C B A
Ii
LF
3 At
AA
Ay Y 82 T a
5
A A
M