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Topic: benzene diazonium chloride + alpha naphthol/ NaOH  (Read 3138 times)

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Offline ricecake

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benzene diazonium chloride + alpha naphthol/ NaOH
« on: December 12, 2014, 10:53:42 PM »
c1ccccc1(n=[n+])+c1cccc2ccccc12  :rarrow: c1ccccc1(n=n-c1cccc2ccccc12)

I couldn't attach the OH to naphthol  using the SMILES after 30 minutes of trying :-\ I was just wondering why the N=N- attached to naphthol at the para position instead of meta
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Offline orgopete

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Re: benzene diazonium chloride + alpha naphthol/ NaOH
« Reply #1 on: December 13, 2014, 06:55:24 AM »
If you did an electrophilic aromatic substitution reaction on a phenol, what regiochemistry would you find?
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Offline ricecake

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Re: benzene diazonium chloride + alpha naphthol/ NaOH
« Reply #2 on: December 13, 2014, 09:04:23 AM »
Phenol will have the para substitution
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Offline orgopete

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Re: benzene diazonium chloride + alpha naphthol/ NaOH
« Reply #3 on: December 13, 2014, 09:54:00 PM »
What might that suggest about the reaction mechanism? What do you think the nitrogen atoms are doing in the reaction?
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