If you had used a 5 solution of NaOH in the washing step ins

If you had used a 5% solution of NaOH in the washing step (instead of 5% NaHCO) and allowed the pH to rise above 12, would your product have remained in the organic layer? Why or why not? Include the equation for the reaction of your product with NaOH to help answer this question. Be sure to use structures in your balanced equation, not just molecular formulae

Solution

If we had used 5% solution of NaOH in the washing step instead of 5% NaHCO3, the pH rose to above 12. All of the product would not have remained in the organic layer. NaOH is a strong base compared to NaHCO3, therefore it would deprotonate the phenolic -OH (present in the organic layer) to sodium salt of phenoxide which goes in water,

Ph-OH + NaOH --> PhONa + H2O

Therefore, washing with NaHCO3 is done and not with NaOH.