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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 $\rm{S_N2}$?

Aditya Dev
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  • 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. – DarrenRhodes Feb 29 '16 at 15:00
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    It is an SN1 reaction, see this earlier answer. – ron Feb 29 '16 at 15:10
  • @ron why does the nucleophilic attack a carbon that does not contain a leaving group? – Aditya Dev Feb 29 '16 at 15:21
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    The initially formed cyclobutyl cation quickly equilibrates with the cyclopropyl carbinyl cation which has positive charge on the necessary carbon. – ron Feb 29 '16 at 15:28
  • Should I mark this question as duplicate @ron ? – Aditya Dev Feb 29 '16 at 15:45
  • I think your question covers the same general ground, so yes, mark it as a duplicate. – ron Feb 29 '16 at 16:06

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