Electromeric Effect

Temporary effect which is observed

in presence of reagents involving
transfer of electrons in an unsaturated
system.

in presence
of reagent + –
X Y X Y
in absence
of reagent
 Electromeric Effect
Addition of HBr to an alkene

R 2 R
1 H H
HBr
C C C—C
H H + – H
H
R
Br
– + +
H
R — CH — CH3 C — CH3
H
Br
Hyperconjugation or no bond resonance
(a) Involves  and  bond orbitals
(b) More the number of hyperconjugative
structures, more will be the stability of
ion or molecule

+ H H
H H H H H
+
+ H–C=C
H–C–C H–C=C–H H C=C
+
H H H H H H H H

Structure of ethyl carbonium ion

Hyperconjugation or no bond resonance
(c) The number of hyperconjugative structures in an alkene is
obtained by the number of C — H bonds attached to the carbon
bonded directly to the double bonded carbon atoms.

H H+ H
–
H
+ C CH
–
CH2
H C CH CH2 H C CH CH2

H H H

H
–
H C CH CH2

H
+
 Significance of Hyperconjugation
H
C
—
3
CH
—C
HC
H2
H
C
—
3C
HC
H
— C
H2
+
H
1–butene (
2h
yp
e
r
co
nj
uga
t
i
ves
t
r
uct
ur
es
)

–
H
C
—
3
C
HCH
—C
H3 H
C
— C
H
—CHC
H2
3
+
H
(
6hy
p
er
co
nj
uga
t
i
ves
t
ru
ct
ur
es
)
2–butene

More stable
 Relative strength of organic acids

O O
R-C O
R-C + +
H R-C
OH O O

Resonance structures
 Class exercise
Allyl isocyanide has
2
(a) 9 bonds and 4 bonds
 
(b) 8 bonds and 5 bonds
 
(c) 8 bonds, 5 bonds and 4 non-bonding electrons
 2 non-bonding electrons
 2 bonds and
(d) 9 bonds,

 

Solution: + –
H2C CH — CH2 — N C
Allyl isocyanide
The compound has 3 p bonds and one lone pair, i.e.
two non-bonding electrons. It also contains 9 s-bonds.

Hence answer is (d).

 Class exercise 3
Among the following which has the most acidic
-hydrogen? 
O O O

(a) CH3CCH2CHO (b) CH3CCH2CCH3

(c) C
H C C
H C O
OCH (d) CH3CHO
3 2 3