1

Dr. N R PANGULURI (NRP)

+91-9738678240
drnrpanguluri@gmail.com

9. GOC 7 Carbanion and Freeradical Page 1

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1.

You are suffering from fever then when will you be happy ?

Fever minimizes

2.

EWG always stabilizes carbanion EDG always destabilizes carbanion

looking for electrons

+M, HC, +I -M, -I

9. GOC 7 Carbanion and Freeradical Page 2

3 Additional Information

looking for electrons

+M, HC, +I -M, -I

9. GOC 7 Carbanion and Freeradical Page 3

4 Hyperconjugation

9. GOC 7 Carbanion and Freeradical Page 4

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3.

strong donating weak donating

strong withdrawing weak withdrawing

9. GOC 7 Carbanion and Freeradical Page 5

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carbanion (suffering from electron density repulsions)

srtong EWG weak EWG

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4.

9. GOC 7 Carbanion and Freeradical Page 7

9 For carbanion

destabilize less destabilizes more

(no effect)

200 km 100 km 50 km
near
very far

robbery from rich house

stabilize less stabilize more

(no effect)
far very near

200 km 100 km 50 km

Stability of carbanions can be explained by

1. Resonance or Mesomeric Effect
2. Hyperconjugation
(possible when resonance supports to carbanions)
3. only Inductive Effect
4. Mesomeric effect and Inductive effect
5. Aromaticity

9. GOC 7 Carbanion and Freeradical Page 8

10 For carbocation

stabilize less stabilize more

(no effect)
200 km 100 km 50 km

Blood donars Patient

destabilize less destabilizes more

no effect

200 km 100 km 50 km

somebody wants kill and Patient

take money

Stability of carbocation can be explained by

1. Resonance or Mesomeric Effect
2. Hyperconjugation & Inductive effect
3. only Inductive Effect
4. HC & M
5. Aromaticity

Dr. N R PANGULURI (NRP)

+91-9738678240
drnrpanguluri@gmail.com

9. GOC 7 Carbanion and Freeradical Page 9

11
Stability of carbanion

1. Mesomeric Effect :

Stability of carbanion :

Stability of carbanions can be explained by

1. Resonance or Mesomeric Effect
2. Hyperconjugation
(possible when resonance supports to carbanions)
3. only Inductive Effect
2. Hyperconjugation :
4. Mesomeric effect and Inductive effect
5. Aromaticity
(possible when resonance supports to carbanions)

(when resonance supports)

(when resonance supports)

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3. only Inductive Effect :

Stability of carbanion :

9. GOC 7 Carbanion and Freeradical Page 11

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Inductive Effect : distance dependent problems

destabilize less destabilizes more

(no effect)

200 km 100 km 50 km

far very near

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Inductive Effect : distance dependent problems

stabilizes less

more

Stability of carbanion :

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Stability of carbanion :

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4. Mesomeric Effect & Inductive effect :

Stability of carbanion :

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5. Aromaticity :

Stability of carbanion :

Stability of carbanion :

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Stability of benzyl carbanions with substituents at o,m,p positions

Carbocation :
NO2, OH, CH3, Cl
Carbanion :
CHO, OCH3, CH3, Br

Stability of carbanion :

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Stability of carbanion :

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Stability of carbanion :

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Needs to modify

destabilizes more
destabilizes less

( ) ( )

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Stability of carbanion :

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(more resonating (less resonating structures)

(aromatic) structures)

1+I
2+I
3+I

Dr. N R PANGULURI (NRP)

+91-9738678240
drnrpanguluri@gmail.com

9. GOC 7 Carbanion and Freeradical Page 23

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Stability of Free radicals

9. GOC 7 Carbanion and Freeradical Page 24

26 looking for electrons

EDG always stabilizes carbocation

EWG always destabilizes carbanion (only -I)

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Mesomeric Effect :

Stability of carbon freeradical :

Stability of carbanion :
Stability of carbanion :

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Hyperconjugation & Inductive effect : HC is preferable

Stability of carbanion :

Inductive effect :

Stability of carbanion :

(Preferable)

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Inductive effect : Distance dependent problems

Stability of carbanion :

destabilize more
destabilize less

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30 Change to carbon freeradical

moderate

(destabilise less)

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Dr. N R PANGULURI (NRP)

+91-9738678240
drnrpanguluri@gmail.com

9. GOC 7 Carbanion and Freeradical Page 30