If potassium tert-butoxide is used in a solution of chloroform and and a strong protic acid like picric acid will the tert-butoxide ion react with picric acid or will it form a dichlorocarbene.

Mechanism for reactions will be much appreciated.

(This is most definitely NOT a homework question! I need to know this to solve my homework problems)

  • $\begingroup$ Well, in both cases, KOtBu acts as a base. If you were a molecule of KOtBu, would you prefer to react with CHCl3 or picric acid? $\endgroup$ – orthocresol Oct 10 '15 at 10:10
  • $\begingroup$ @orthocresol from what I know, I would react with picric acid because it has a pKa of around .38 ( I think?), much lower than that of chloroform. But I wanted to know if there was some other mechanism that I wasn't aware of which would force it to react with CHCl3 to form a dichlorocarbene. $\endgroup$ – Ayan Gangopadhyay Oct 10 '15 at 11:28
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    $\begingroup$ Depends if you had more equivalents of KOtBu than picric acid.Even if you have some chloroform deprotonation, the protonation from picric acid is so much faster than loss of Cl-. $\endgroup$ – Beerhunter Oct 10 '15 at 11:34

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