What are the products formed in the reaction of cyclobutylamine with $\ce{NaNO2}$ and $\ce{HCl}$?

I thought the answer was only cyclobutanol. But the answer given says the product contains cyclopropyl carbinol as well. How does the second product form?

This is basically a diazotization reaction which results in the conversion of $\ce{- NH2}$ to $\ce{- N2^+Cl-}$ which is a good leaving group. Then water molecules will attack the carbon containing the leaving group. Is the reaction $\rm{S_N1}$ or $\rm{S_N2}$?

  • $\begingroup$ The water is attacking the carbon next to the one that has the diazonium cation on it, this leads to a bond migration and subsequent loss of nitrogen. As to whether the reaction occurs in the order described is another matter. $\endgroup$ Feb 29, 2016 at 15:00
  • 3
    $\begingroup$ It is an SN1 reaction, see this earlier answer. $\endgroup$
    – ron
    Feb 29, 2016 at 15:10
  • $\begingroup$ @ron why does the nucleophilic attack a carbon that does not contain a leaving group? $\endgroup$
    – Aditya Dev
    Feb 29, 2016 at 15:21
  • 3
    $\begingroup$ The initially formed cyclobutyl cation quickly equilibrates with the cyclopropyl carbinyl cation which has positive charge on the necessary carbon. $\endgroup$
    – ron
    Feb 29, 2016 at 15:28
  • $\begingroup$ Should I mark this question as duplicate @ron ? $\endgroup$
    – Aditya Dev
    Feb 29, 2016 at 15:45


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