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HO OH H H O - . .. Electron Replacing Group O H +

Fragmentation reactions involve the cleavage of a carbon-carbon single bond and require an electron-withdrawing group and electron-donating group. If these groups are adjacent, fragmentation will result in migration, but if separated it will result in fragmentation. For fragmentation to occur, the reaction groups need to have a 1,4-relationship and be anti-periplanar. Some examples of reactions that can be viewed as fragmentations are the reverse of aldol condensation, decarboxylation of beta-ketoacids, and elimination from unsaturated acids.

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53 views1 page

HO OH H H O - . .. Electron Replacing Group O H +

Fragmentation reactions involve the cleavage of a carbon-carbon single bond and require an electron-withdrawing group and electron-donating group. If these groups are adjacent, fragmentation will result in migration, but if separated it will result in fragmentation. For fragmentation to occur, the reaction groups need to have a 1,4-relationship and be anti-periplanar. Some examples of reactions that can be viewed as fragmentations are the reverse of aldol condensation, decarboxylation of beta-ketoacids, and elimination from unsaturated acids.

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BHAAJI0001
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Fragementations are reactions involving cleavage of C - C single bond.

It requires electron pull


and electron push. If the source and sink of electrons are adjacent as in the case of pinacol and
pinacolon rearrangement, there will be migration and if they are separated, there will be fragmenta-
tion. Reaction groups should have 1, 4- relationship, and anti- periplanar. Reverse of aldol con-
densation, decarboxylation of - ketoacid, and unsaturated acids may be viewed as elimination or
fragmentation.

HO OH
H
+
H O
. .
..
Electron
replacing
group
O H
+
H
Electron
Withdrawing
group
CHO
14.
OH
OT s
(X)
Base
(A)
OH
(B)
OH
(C)
O
(D)
O
Sol. C

OH
O Ts
Base
-H O
2
O Ts
O
15.
CH
3
OSO CF
2 3
(I) HBR
2
(II) OH
- (Y)
The Product Y is

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