100% found this document useful (2 votes)
405 views21 pages

Mesomeric Effect

The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

Uploaded by

Awais Arshad
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
100% found this document useful (2 votes)
405 views21 pages

Mesomeric Effect

The most acidic hydrogen is present in compound (c) as it has an α-hydrogen to a carbonyl group with no alkyl substitution. The order of acidity is: (c) > (a) > (d) > (b) Hence, the most acidic hydrogen is present in option (c).

Uploaded by

Awais Arshad
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
You are on page 1/ 21

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

You might also like