Organic Chemistry - Decarboxylation

24

eureka123 ·2009-10-06 03:40:18

but in decrboxylation reaction carbanion is formed naa ???

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24

eureka123 ·2009-10-06 10:08:25

no problemo dude...

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1

aieeee ·2009-10-06 10:06:41

oops. very sorry. hv edited it.

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24

eureka123 ·2009-10-06 08:47:02

thx..organic for confirmation...

maybe aieeee made just that sign mistake...

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19

Debotosh.. ·2009-10-06 08:44:39

yes to all who say that carbanion is the intermediate ! bridgehead carbanion is the most unstable in this context...hence (a) never undergoes decarboxylation !
@msp...you should not have pinked that post without confirmation...gives others a wrong concept here !

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1

RDX ·2009-10-06 07:49:24

Yeah, I think carbonanion will be formed in this case.

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24

eureka123 ·2009-10-06 03:55:39

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24

eureka123 ·2009-10-06 03:49:16

no no...............as far as i know its carbanion formation...

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3

msp ·2009-10-06 03:45:09

well eure thermolysis is a way to produce free radicals,i confirmed it in the peter sykes,(free radical chapter).

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1

Aditya Balasubramanyam ·2009-10-05 11:07:59

is it c ??

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3

msp ·2009-10-06 03:38:16

eure remove the + sign and put a dot in that place,nothing more.and we know the free radical is sp2 hybridised as like a carbocation.

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24

eureka123 ·2009-10-06 03:36:10

can u explain ur point with a figure msp ??

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3

msp ·2009-10-06 03:27:36

actually i think free radical will be formed, and not carbocation formation.Neways the free radical formed shud be sp2hybridised,and it shud have a planar structure,so the intermediate is extremely unstable.

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1

aieeee ·2009-10-06 01:37:14

if decarboxylation occurs in a) , then -CO₂ would be eliminated forming bridgehead carbanion as transition intermediate , which is very unstable.

thus answer is a.