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Inductive Effect
Inductive Effect
Inductive Effect
IN DUCTIVE EFFECT
Inductive effect is the polarization of shared _pair (covalently bonded pair) of electrons towards more
electronegative atoms. Let us consider a molecule.
888+ 88+ 8+ 8-
C-+--C-+-- C--+--c
r:r A permanent effect
r:r The electrons never leave their original atomic orbital.
r:r Its magnitude (i.e., electron withdrawing or donating power) decreases with increase in distance.
r:r There occurs partial movement of shared pair of electrons.
r:qo 'This effect is additive in nature, i.e. two ele'ctronegative atoms exert greater induction effect than one atom
of greater electronegativity from the same position.
142 I Advance Theory in ORGAN IC CHEMISTRY
I d · . • · to 2 types.
n uctive effect showing groups can be d1v1ded in t
Inductive effec
-I )
+I
withdrawing group
(electron
(electron donating group)
INDUCTIVE EFFECTS
1nductive Effect (I Effect of Groups)
El I) For examP 1e,
ectron donating groups show positive inductive effect(+ ·
-T>-D>-H
-N-R>-0
-Se> - §
-C(CH 3h > -CH(CH 3)2 >- CH2-CH3 >- CH3
- i -
-O >-C-0
Electron withdrawing groups show negative inductive effect (-1). For example,
+ +
-OR2 >-NR3 -F >-OR >-NR2 >-CR3
+ + + + 0 0
- NCH3 >- P- CH3 >-As-CH3 >-Sb-CH3 II II
I I I I -S- R >- S-R >-S-R
CH3 CH3 CH3 CH3 II
0
-SIR3 >-GeR3
+ +
-OR2 >-0R - C •NH >-CH= NH2 >-CH -NH,
2
+ +
-SR2 >-SR - NH3>-NH2
-o>-CH=CH2
7_n ~
.
i @ ";\ (±) •· - , -
CH
3
2-hybrnica,t,on '' ..1,;
> CHz=r:s;Ji~ridcart>on -~,,
· sp2-hybridised carbon is less EN sp-hybrid carbon is more electronegative
1• more stable - less stable
(d) Stability of-/t;lkyl, Viny{ a~d'Acetyienic Carbani~~s ·: •
·,_ 1 e f..__,r 6 I\ e
·CH:i,- tH2 . -CH2=tH -- , _ '> CH=C
ORDER OP STABILITY
The order of stability of carbocations, carbanions and car~on ra~icals bearing electron donating (+ I) alkyl groups,
R, is as follows. (Free radicals will be formed by homolyt1c fission) _
Tertiary Secondary Primary Methyi
three t ,l groups_,, two + groups !
one + I groups no + I groups
R R R H
Cation ll@ ll@ ll@ I@
C > ~C"-'. > C > C
Stability R>V ~R R1/ ')( H H/ '--H H/ '--H
R
Anion
R
lie lie < <
.. , < x}c,
Stability
R>VC~R R H
R
R ll •
.Radical ll. > ~c > >
Stability R 1/ '--H
R>Vq~R
1144 I Advance Theory in ORGAN IC CBEMJSTRY whereas carbocatlons can b
-M groups), e
Carbanions can be stabllised by electron-withdrawing groups (-I. ·
stabilised by electron-donating groups (+i +M groups).
Solved Exam le
Which of the side chain attached to benzene ring have + I effect
's~ ,
0~ /OH
CH 3
(1
CH
I
O (iv)
~o (iii)
(i)v (ii)
~
Solved Example
'X' = Number of compound having -I group directly attached to benzene.
~COOH
~S03H ~C='N · '~# '
Sol.
Find the valu~ of 'X' ?
@f-1
Sox=?
Inductive Effect I 145
I '
Answers
~o. h : ---.&.;.....i.:~i.a....- - - " '
1. (:a) -"- I -
1
(h) +I
(e) -I ' , (f) ~IJr
('I
(i) +i U) -I (k) +I (I) -I
(o) -I (p) -I
(m) +I (n) -I
(q) _ 1 (r) None (s) -I (t) None