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problem in wolf kishner mechanism
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Topic: problem in wolf kishner mechanism (Read 1984 times)
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ABA2015
Regular Member
Posts: 44
Mole Snacks: +0/-2
problem in wolf kishner mechanism
«
on:
October 08, 2014, 04:48:20 AM »
hi all
I can't understand why in organic mechanisms some times an atom such as N can have 4 valence and indicates as N
+
but sometimes not, for example in wolf Kirchner mechanism as follow, but in manich reaction N can be positive with 4 valence
«
Last Edit: October 08, 2014, 05:04:56 AM by ABA2015
»
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ABA2015
Regular Member
Posts: 44
Mole Snacks: +0/-2
Re: problem in wolf kishner mechanism
«
Reply #1 on:
October 08, 2014, 05:03:07 AM »
sorry I could not attach the mechanism
the known intermediate of wolf kishner is for example in acetone reaction with hydrazine
(CH3)2-HC-
N
=NH
why this one is not observed
(CH3)2-HC=
N
+
=NH
«
Last Edit: October 08, 2014, 05:14:58 AM by ABA2015
»
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mjc123
Chemist
Sr. Member
Posts: 2069
Mole Snacks: +302/-12
Re: problem in wolf kishner mechanism
«
Reply #2 on:
October 08, 2014, 05:19:06 AM »
Because (CH
3
)
2
HC=N
+
=NH would have a 5-valent carbon. (and where is the negative charge?)
In H
2
C
+
-NMe
2
the carbon has six electrons and a vacant p orbital, so N can donate its lone pair to form a pi bond, and the formal + charge shifts from C to N.
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problem in wolf kishner mechanism