f 1-phenylazo-2-naphthol (or Sudan I), phenyldiazonium reacts with β-naphthol. Draw the resonance structures of the intermediate formed when the diazonium ion attacks a) carbon 1 and b) carbon 3 of β-naphthol. Based on the resonance structures, explain why attack on carbon 1 is preferred

f 1-phenylazo-2-naphthol (or Sudan I), phenyldiazonium reacts with β-naphthol. Draw the resonance structures of the intermediate formed when the diazonium ion attacks a) carbon 1 and b) carbon 3 of β-naphthol. Based on the resonance structures, explain why attack on carbon 1 is preferred

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section19.3: Claisen And Dieckmann Condensations

Problem 19.6P

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Question

In the synthesis of 1-phenylazo-2-naphthol (or Sudan I), phenyldiazonium reacts with β-naphthol.

Draw the resonance structures of the intermediate formed when the diazonium ion attacks a) carbon 1 and b) carbon 3 of β-naphthol. Based on the resonance structures, explain why attack on carbon 1 is preferred.

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