Question

8. The Pincel rearrane e Pinacol rearrangement was discovered in 1880 and involves an interesting transformation of a do compound to a ketone compound in acidic solution Propose a mechanism for the transformation beow con H2O in H2O 0 in 40 g 9. A two-step synthesis of compound A from butane is shown. Draw the structure of the product from the first step and provide a mechanism for its formation. Your mechanism must show all steps of the reaction NaCN DMF Page 5

Answer 1

H-O 1-042 04 14,0 Ring expansion 1-HⓇ qa80 OmF mechanism: 37.5o hiya By for is + Her n ona tor egter Teas e

w g two reactions proceed through an S2 mechanism Determine the likely product for each and match the 1H NMR spect NMR spectrum below to the product of one of the reactons Show your assignments for ALL below to the product of o NMR peaks to explain your conclusions. CHy-t, K,Co, DMF 2H2H o 5 ppm Page 4