Question

4. Enol ether 10 can be hydrolyzed under acidic conditions to give products 11 and 12. acidic ER aqueous conditions + HOR' a) Draw a mechanism for the enol ether hydrolysis reaction. b) The rates for the hydrolysis of enolether 10 were determined. Find below a graph with the reaction rates in H20 and D20 in the pH range of 3 to 4.5 (o for the reaction in H20 and for the reaction in D-0). Designate the slowest step in your mechanism with the word SLOW (5-10 logik 30 35 40 45 60 65 50 55 PH/PD c) Explain your reasoning with the concept of kinetic isotope effects.

Answer 1

DATE Mechanism :- HOR +HCL HR Po 1RI I slow Slow H2O: 1 step. Aldehyde alcohol 127 Here enol ether Elact with acid in presence of water giver aldehyde & alcohol. This reaction. is called acid cotolysed hydrolysis reaction. Atrack of water on elecbon deficient carbon is slow slep. O Instead of water if we use D20 then rake of reaction decreases. It shows that this step is slow slep. slow 7 I too oto 604