Question

4. Alan Kene (his friends call him Al) is exploring a variety of SN2 reactions in the lab. One day he decides to undertake the reaction shown below. Once the reaction was complete he collected 'HNMR data on the crude product, he was shocked to see the lack of an OH signal in the NMR data (or IR -not provided), so he knew the reaction did not go as planned. To help deduce the structure of the actual product formed he collected mass spec data, which indicated a molecular formula of C4HeO2 4a). Draw the mechanism for the intended SN2 reaction Al was attempting to achieve 4b). Using the NMR data below, determine the structure of Al's mystery product. Things to think about: Given the reagent and the substrate are there other possibilities? Is there more than one reactive site in the substrate? SN2 2H 2H PPM

Answer 1