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Inductive Effect Or Transmission Effect

Category : JEE Main & Advanced
(1) When an electron withdrawing (X) or electron-releasing (Y) group is attached to a carbon chain, polarity
is induced on the carbon atom and on the substituent attached to it. This permanent polarity is due to
displacement of shared electron of a covalent bond towards a more electronegative atom. This is called
inductive effect or simply as I - effect.
C − C − C − C Non polar
+ + + + −
δδδδ δδδ δδ δ δ
C → −C → −C → −C → −X
− − − − +
δδδδ δδδ δδ δ δ
C − ← C − ← C − ← C − ← Y
Free(2) Carbon-hydrogen bond is taken as a standard of inductive effect. Zero effect is assumed for this bond.
Videos
Atoms or groups which have a greater electron withdrawing capacity than hydrogen are said to have–I
effect whereas atoms or groups which have a greater electron releasing power are said to have +I effect.
C ON H2 > F > Cl >Br > I > OH > OR > N H2 > C 6 H5 >H
−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−→
I power of groups in decreasing order with respect to the ref erenceH
ter.alkyl >sec.alkyl >pri.alkyl >
−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−→
+ I power in decreasing order with respect to the ref erenceH
C H3 −C H2 −C H2 −C H2 −>C H3 −C H2 −C H2 −>C H3 −C H2 −
−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−→
+I power in decreasing order in same type of alkyl groups
(3) Applications of Inductive effect
(i) Magnitude of positive and negative charges : Magnitude of +ve charge on cations and magnitude of
–ve charge on anions can be compared by +I or – I groups present in it.
1
Magnitude of +ve charge ∝ ∝ −I power of the group.
+I power of the group
1
Magnitude of −ve charge ∝ ∝ +I power of the group.
−I power of the group
(ii) Reactivity of alkyl halide : +I effect of methyl group enhances – I effect of the halogen atom by
repelling the electron towards tertiary carbon atom.
C H3 C H3
↓ ↓
H2 C → C → X > H3 C → C H → X
↑
C H3
> C H3 → C H2 → X > C H3 → X
Tertiary > Secondary > Primary > Methyl
(iii) Relative strength of the acids :


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(a) Any group or atom showing +I effect decreases the acid strength as it increases the negative charge
on the carboxylate ion which holds the hydrogen rmly. Alkyl groups have +I effect.
Thus, acidic nature is,

H C OOH > C H3 C OOH > C 2 H5 C OOH > C 3 H7 C OOH > C 4 H9 C OOH
−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−→
+ I effect increases, so acid strength decreases
Formic acid, having no alkyl group, is the most acidic among these acids.
(b) The group or atom having −I effect increases the acid strength as it decreases the negative charge on
the carboxylate ion. Greater is the number of such atoms or groups (having −I effect), greater is the acid
strength.
Thus, acidic nature is,

C C l 3 C OOH >C H C l 2 C OOH >C H2 C lC OOH >C H3 C OOH
Trichloro Dichloro Monochloro Acetic acid
acetic acid acetic acid acetic acid

←−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−
( Inductive effect increases, so acid strength increases)
(c) Strength of aliphatic carboxylic acids and benzoic acid

Free
VideosR → C OOH C6 H6 ← C OOH
↑ ↑
+I group −I group
Hence benzoic acid is stronger acid than aliphatic carboxylic acids but exception is formic acid. Thus,
H C OOH > C6 H5 C OOH > RC OOH
→
Acid strength in decreasing order
Decreasing order of acids :
N O2 C H2 C OOH > F C H2 C OOH > C lC H2 C OOH > BrC H2 C OOH .
F3 C − C OOH > C l3 C − C OOH > Br 3 C − C OOH > I 3 C − C OOH .
C H3 OH > C H3 C H2 OH > (C H3 ) C H OH > (C H3 ) C OH

2 3
.
M ethyl Ethyl I so−propyl T ert−butyl
alcohol Alcohol alcohol alcohol
As compared to water, phenol is more acidic (−I effect) but methyl alcohol is less acidic (+I effect).
(vi) Relative strength of the bases (Basic nature of −N H2 )

The difference in base strength in various amines can be explained on the basis of inductive effect. The +I
effect increases the electron density while −I effect decreases it. The amines are stronger bases than
N H3 as the alkyl groups increase electron density on nitrogen due to +I effect while C lN H2 is less
basic due to −I effect. “So more is the tendency to donate electron pair for coordination with proton, the
more is basic nature, i.e., more is the negative charge on nitrogen atom (due to +I effect of alkyl group), the
more is basic nature”.
Thus, the basic nature decreases in the order;
(C2 H5 ) N H > C H3 C H2 N H2 > C H3 N H2 > N H3 > C lN H2

2
Diethyl Ethyl Methyl Ammonia Chloro
amine amine amine

amine
The order of basicity is as given below;
Alkyl groups (R-) Relative base strength

C H3 R2 N H > RN H2 > R3 N > N H3
C2 H5 R2 N H > RN H2 > N H3 > R3 N
(C H3 ) C H RN H2 > N H3 > R2 N H > R3 N

2
(C H3 ) C N H3 > RN H2 > R2 N H > R3 N

3
The relative basic character of amines is not in total accordance with inductive effect (t > s > p)
Free but it is in the following order: Secondary > Primary > Tertiary. The reason is the steric hindrance
Videos existing in the t-amines.
In gas phase or in aqueous solvents such as chlorobenzene etc, the solvation effect, i.e., the
stabilization of the conjugate acid due to H -bonding are absent and hence in these media the
basicity of amines depends only on the +I effect of the alkyl group thus the basicity of amines
follows the order : 3 o > 2 o > 1 o > N H3 .
(vii) Basicity of alcohols : The decreasing order of base strength in alcohols is due to +I effect of alkyl
groups.
(C H3 ) C OH > (C H3 ) C H OH > C H3 C H2 OH > C H3 OH

3 2
o o o
(3 ) (2 ) (1 )
(viii) Stability of carbonium ion : +I effect tends to decrease the (+ve) charge and −I effect tends to
increases the +ve charge on carbocation.
⊕ ⊕ ⊕ ⊕
(C H3 ) C > (C H3 ) C H > C H3 C H > CH
3 2 2 3
(ix) Stability of carbanion : Stability of carbanion increases with increasing −I effect.

− −
C H − > C H3 C H − > (C H3 ) C H > (C H3 ) C
3 2 2 3
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Inductive Effect Or Transmission Effect

(3) Applications of Inductive effect

Tertiary > Secondary > Primary > Methyl

(iii) Relative strength of the acids :

Thus, acidic nature is,

Thus, acidic nature is,

acetic acid acetic acid acetic acid

(c) Strength of aliphatic carboxylic acids and benzoic acid

Decreasing order of acids :

N O2 C H2 C OOH > F C H2 C OOH > C lC H2 C OOH > BrC H2 C OOH .

F3 C − C OOH > C l3 C − C OOH > Br 3 C − C OOH > I 3 C − C OOH .

C H3 OH > C H3 C H2 OH > (C H3 ) C H OH > (C H3 ) C OH

(vi) Relative strength of the bases (Basic nature of −N H2 )

Thus, the basic nature decreases in the order;

(C2 H5 ) N H > C H3 C H2 N H2 > C H3 N H2 > N H3 > C lN H2

amine amine amine

The order of basicity is as given below;

Alkyl groups (R-) Relative base strength

C2 H5 R2 N H > RN H2 > N H3 > R3 N

(C H3 ) C H RN H2 > N H3 > R2 N H > R3 N

(C H3 ) C N H3 > RN H2 > R2 N H > R3 N

(C H3 ) C OH > (C H3 ) C H OH > C H3 C H2 OH > C H3 OH

(ix) Stability of carbanion : Stability of carbanion increases with increasing −I effect.

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