In the two-pot synthesis, which acts as the nucleophile, 2-naphthol or phenyldiazonium?

Solomons et al. (2014) says that phenyldiazoium is weakly electrophilic. Yet in the questions to be answered in our laboratory manual, it asks for resonance structures on the attack of phenyldiazonium on carbon 1 and carbon 3 of beta-naphthol. This is the mechanism I can find in the books. I'm confused. I can't seem to find a mechanism wherein phenyldiazonium acts as a nucleophile in the internet or in my books.

  • $\begingroup$ Maybe you can draw a mechanism yourself and add it to your question? If you're looking for a free molecule editor: I'm using BKChem for my posts on Chem.SE. $\endgroup$ Commented Oct 31, 2016 at 18:17
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    $\begingroup$ Even though arrows are always drawn to represent nucleophilic attack, the word "attack" can in general refer to electrophilic attack as well, so there might not be any real contradiction here. $\endgroup$ Commented Oct 31, 2016 at 18:25
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    $\begingroup$ Following up on @orthocresol's comment, we typically learn the term 'attack' with respect to nucleophiles (e.g., in SN2 reaction), but 'attack' can be used for electrophiles as well. $\endgroup$
    – jerepierre
    Commented Oct 31, 2016 at 18:28
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    $\begingroup$ Some pedantry: your second arrow should really be a $\ce{<->}$, not a $\ce{<=>}$. Those are two resonance forms of naphthol which are not being rapidly interconverted. $\endgroup$ Commented Oct 31, 2016 at 18:47

1 Answer 1


It was mentioned in the comments but I shall mention it again.

Attack does not have to mean nucleophilic attack. In your case, the attack is electrophilic, the electrophile phenyldiazonium attacking the naphtholate.


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