Rearrangement Reactions vikram choudhary

Rearrangement Reactions

1. Presented by: Vikram Choudhary
M. Pharm First Semester, School of Pharmacy, DAVV, Indore

2. Content of Presentation-
 What is Rearrangement ?
 Types of Rearrangement
1. Rearrangement to Electron Deficient Carbon
2.Rearrangement to Electron Deficient Nitrogen
3.Rearrangement to Electron Deficient Oxygen
4.Rearrangement to Electron-Rich Carbon
5.Aromatic Rearrangements

3. REARRANGEMENT REACTIONS
• A rearrangement reaction is a broad class of organic
reactions where the carbon skeleton of a molecule is
rearranged to give a structural isomer of the original
molecule. Often a substituent moves from one atom to another
atom in the same molecule .
• Rearrangement reactions involve the migration of a group or
an atom from one center (migration origin) to another
(migration terminus) within the same molecule.
What is Rearrangement ?

4. Y Z X Y
W
ZX
W In the above-mentioned generalized representation,
atom-X is migration origin from where the migrating
group “W” moves to atom-Y (migration terminus )
REARRANGEMENT REACTIONS
What is Rearrangement ? Cont’d

5. Types of Rearrangements
1.Rearrangement to Electron Deficient Carbon
2.Rearrangement to Electron Deficient Nitrogen
3.Rearrangement to Electron Deficient Oxygen
4.Rearrangement to Electron-Rich Carbon
5.Aromatic Rearrangements
5 Types of Rearrangements-
REARRANGEMENT REACTIONS

6. Mechanism
1. Rearrangement to Electron Deficient Carbon
REARRANGEMENT REACTIONS R''
R'''
R'
R
OH
R''
R'''
R
R'
O
H
+
H
H

7. Mechanism






REARRANGEMENT REACTIONS
1. Rearrangement to Electron Deficient Carbon
Cont’d R''
R'''
R'
R
OH
R''
R'''
R
OH
2
H
R'
-H
2O
R''
R'''
R'
R
R''
R'''
R
OH
2
R''
R'''
R
R'
H

8. Mechanism


REARRANGEMENT REACTIONS
1. Rearrangement to Electron Deficient Carbon
Cont’d

9. Mechanism
REARRANGEMENT REACTIONS
1. Rearrangement to Electron Deficient Carbon
Cont’d

10. Mechanism
REARRANGEMENT REACTIONS
1. Rearrangement to Electron Deficient Carbon
Cont’d

11. REARRANGEMENT REACTIONS
2. Rearrangement to Electron Deficient Nitrogen
Mechanism

12. Mechanism
REARRANGEMENT REACTIONS
2. Rearrangement to Electron Deficient Nitrogen
Cont’d

13. Mechanism
REARRANGEMENT REACTIONS
3. Rearrangement to Electron Deficient Oxygen

14. Mechanism
REARRANGEMENT REACTIONS
3. Rearrangement to Electron Deficient Oxygen
Cont’d

15. Mechanism
REARRANGEMENT REACTIONS
4. Rearrangement to Electron - Reach Carbon

16. Mechanism
REARRANGEMENT REACTIONS
4. Rearrangement to Electron - Reach Carbon
Cont’d

17. Mechanism
REARRANGEMENT REACTIONS
5. Aromatic Rearrangements

18. Mechanism
REARRANGEMENT REACTIONS
5. Aromatic Rearrangements
Cont’d

19. Mechanism
REARRANGEMENT REACTIONS
5. Aromatic Rearrangements
Cont’d

20. Mechanism
REARRANGEMENT REACTIONS
5. Aromatic Rearrangements
Cont’d