Question enter image description here


1.Wolf kishner would reduce double bond oxygen to alkane.

2.Also since water is present acetal should break.

3.SnAr doesn't seems possible due to adjacent bulky groups.

So according to me answer should be C But why am I wrong? Please help.

  • 2
    $\begingroup$ Acetals are stable to aq base. They need acidic conditions for removal. SNAr seems a very real possibility, the Cl is doubly activated. $\endgroup$
    – Waylander
    Apr 29, 2020 at 6:57
  • $\begingroup$ But wouldn't the bulkynadjacent group reduce SnAr $\endgroup$ Apr 29, 2020 at 12:00
  • 1
    $\begingroup$ Not that much. The potential nucleophiles are fairly small and potentially intramolecular. Is this a reaction drawn from a literature example? It would not surprise me if this gave a benzopyrazole. $\endgroup$
    – Waylander
    Apr 29, 2020 at 12:21
  • 1
    $\begingroup$ See step 4 --> 5 here: chemistry.stackexchange.com/questions/124901/… $\endgroup$
    – user55119
    Apr 29, 2020 at 15:29
  • $\begingroup$ Check the temperature required for the Wolff -Kishner reduction and then determine if you think nucleophilic substitution could occur given the other functional group on the ring. $\endgroup$
    – Beerhunter
    May 6, 2020 at 18:18


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