Given is following nucleophilic reaction with product A. Draw the mechanism of the reaction and give the structure formula of A. Nucleophilic reaction

Here is my solution, I am sure it is not right. Could you help me, step by step to understand this reaction. Solution

  • 2
    $\begingroup$ OH isn't a great nucleophile but is a good base. What is the most acidic proton in the starting material? $\endgroup$ – Waylander Jul 31 '17 at 17:59
  • $\begingroup$ I think the H by OH,becauce it has a pKa from 10, and the N has a pKa bigger than 10. So the NaOH take the H and we have $O^-$ $\endgroup$ – Bruce Dachar Jul 31 '17 at 18:11
  • 1
    $\begingroup$ Correct! And phenoxide is a good nucleophile. $\endgroup$ – Waylander Jul 31 '17 at 18:28
  • $\begingroup$ ok, so the phenoxide will replace the Br. $\endgroup$ – Bruce Dachar Jul 31 '17 at 18:36
  • 2
    $\begingroup$ Exactly so. The reaction ethylates the phenol $\endgroup$ – Waylander Jul 31 '17 at 18:44

With the help from Waylander (s.o.) we get the following mechanism.


| improve this answer | |
  • 2
    $\begingroup$ Looks correct to me $\endgroup$ – Waylander Jul 31 '17 at 18:48

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.