# Nucleophilic Substitution with ethyl bromide and NaOH

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

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

• OH isn't a great nucleophile but is a good base. What is the most acidic proton in the starting material? – Waylander Jul 31 '17 at 17:59
• 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 $O^-$ – Bruce Dachar Jul 31 '17 at 18:11
• Correct! And phenoxide is a good nucleophile. – Waylander Jul 31 '17 at 18:28
• ok, so the phenoxide will replace the Br. – Bruce Dachar Jul 31 '17 at 18:36
• Exactly so. The reaction ethylates the phenol – Waylander Jul 31 '17 at 18:44