wolf kishner rxn

[boomboom2dolla]

Does anybody know why the OH attack the H from the Nitrogen rather than a H from one of the methyl?
thanks for the help

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[sciencegod]

its because of the stabilizing effedts of the resonance structures. by attancking the h of the nh, 3 resonacne forms are produced. hope rhat helps.

 

[joonkimdds]

how do we know how many resonance structures will be produced?
I think attacking H of C will also form resonance structure but just one kind i think,.

 

[IdahoDoc]

It also has to deal with the PKa values of both the pka of a methyl is about a 60 and the PKa on the Nitrogen is around 18 to 20 so it is much easier to remove from the nitrogen then the methyl. The difference in PKa is due to the resonance of the Nitrogen portion of the compound as was stated. earlier.