Organic Chemistry - Schmidt Rxn

24

eureka123 ·2009-11-01 05:44:18

http://en.wikipedia.org/wiki/Schmidt_reaction

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eureka123 ·2009-11-01 05:44:31

see the second reaction there[1]

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11

Gone.. ·2009-11-01 05:50:54

ya thats there in books also..( rxn wid ketones is 2nd one right ??)..try this out. What u think will be the final product here ??

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24

eureka123 ·2009-11-01 05:56:44

is ans something diff ??

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11

Gone.. ·2009-11-01 06:03:18

ya..hope u have noticed there are 2 mole of N3H

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39

Pritish Chakraborty ·2009-11-01 07:35:49

I think the ans will be an 8 membered ring (two rearrangements)

If you have a doubt, I'll post the mechanism..its quite lengthy.

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Gone.. ·2009-11-01 17:53:12

no thats not the ans given in the book..shud i tell the ans ??

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24

eureka123 ·2009-11-01 18:39:08

my ans too is same as pritish...

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eureka123 ·2009-11-01 18:45:15

here is the mech

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Pritish Chakraborty ·2009-11-01 21:25:19

Also possibly after one rearrangement, the second mole of hydrazoic acid will attack the carbocation(HSAB theory), the diazonium ion will leave and then another rearragement takes place to accommodate the second nitrogen in the ring. Then water can attack on the second carbocation.