[go: up one dir, main page]
Scribd
Upload
16 views15 pages

Goc 3

Uploaded by

jokescom5
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
16 views15 pages

Goc 3

Uploaded by

jokescom5
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 15

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

You might also like