Inductive
effect
+I -effect –I-effect
–I -effect
The atom or group withdraw electrons form the carbon chain is said to
have –I-effect.
−
𝜹+ 𝜹+
𝟐 𝜹+
𝟏
(EN)C < (EN)Z
𝟑
C C C Z
Examp e
-I groups
+ve charge Neutral &
more EN
⊕
–NR3 –NH2
⊕
–SR2 –OH
⊕
–NH2 –SH, etc.
Partial +ve
charge
–NO2
𝛿– O
– C – H , etc.
𝛿+
Factor affecting –I group
Generally as electronegativity of group/atom increases (greater than
carbon), –I effect increases.
-I ∝ E.N. ∝ % s character
Hybridisation % s-character EN value
sp3 25 2.5
sp2 33.33 2.75
sp 50 3.25
Order of –I Csp > Csp2 > Csp3
Overall strength of –I group
+ ve charge > partial +ve charge > neutral
⊕ ⊕ ⊕
−NR3 > −SR2 > −NH3 > −NO2 > −SO2R > −CN > −SO2Ar > −COOH > −F
>−Cl > −Br > −I > −OAr > −COOR > −OR > −COR > −SH > −SR > −OH > −C≡CR
> −Ar > −HC=CR2
NOTE
Strength of –I group of 2nd period:
F > O(sp2) > N(sp) > O(sp3) > N(sp2) > C(sp) > N(sp3) > C(sp2) > C(sp3)
NOTE
For comparison of –I group of alkyl chain
D N P
Distance No. of Power of that
group group
F NO2
–C –C –C < –C –C –C
F NO2
–C –C –C > –C –C –C
Cl Cl F
–C –C –C > –C –C –C
Types of Intermediate
Carbocation Carbon free radical Carbanion
• ⊖
CH3 CH3 CH3
Bond pair 3 3 3
Lone pair 0 0 1
Vacant orbital 1 0 0
Unpaired e- 0 1 0
Magnetic Property Dia Para Dia
Valence e- 6 7 8
Octet status Incomplete Incomplete Complete
Types of Intermediate
Carbocation Carbon free radical Carbanion
• ⊖
CH3 CH3 CH3
e- status e¯ deficient e¯ deficient e¯ rich
Stabilized by +I +I -I
Hybridization sp2 sp2 sp3
Bond angle 1200 1200 1070
Geometry Trigonal planar Trigonal planar Pyramidal
Nature Neither lewis acid
Lewis acid Lewis base
nor lewis base
Application of Inductive effect
Stability of Intermediate
(A) Carbocation
1
Stability of carbocation ∝ +I– Effect ∝
−I –Effect
Examp e
1.) MeCH2 < Me2CH < Me3C
2.) < <
F Cl
3.) < <
4.) CH3 < CD3 < CT3
(B) Free Radical
EDG always increases the stability, but EWG may decreases or increases
the stability of free radical
-I effect only decreases the stability of free radical.
1
Stability of Free Radical ∝ +I– Effect ∝
−I –Effect
Examp e
1.) MeCH2 < Me2CH < Me3C
2.) < <
F Cl
3.) < <
(C) Carbanion
∝
Stability of Carbanion ∝ -I– Effect 1
+I –Effect
Examp e
⊖ < ⊖ ⊖
1) MeCH2 Me2CH Me3C
<
⊖ ⊖ ⊖
2) CH3-C < CH2= CH < CH≡C
3) CH3CH2CH–O¯ < CH3CHCH2–O¯
CH3 CH3
Examp e
F NO2
−
O < O−
4)
⊖ ⊖ ⊖
5) H2C — NO2 < HC — NO2 < O2N — C — NO2
NO2 NO2
