Question

Page 3 12. Do either A or B, but only do one of them! Write a rational synthetic sequence for one of the two transformations shown below, using any catalysts or any other organic or inorganic compounds needed. Be sure to show the chemical structures of all intermediate compounds formed on your way to the final structure. A CH₂-C-CH₂-COOH CH₃- Ć -OH -estens 13. (16 pts) Compound P was a pleasant smelling, colorless liquid with a boiling point of 218 degrees C. It had no effect on either red or blue litmus paper. A mass spectrum of Compound P showed a molecular ion at 134 with a base peak at 105 When i . Ald

Answer 1

i i W prsa. LIAIHA Toi H3C0CH3 o H OH OH Acetic anhydride 10 i CH3 Protection of ketone Protection of Reduction of carboxylic acid acetal hydrolysis H30* erotato CH3 H3C MgBr CH3 H3C COOH -CH3 NBS / hv Br Mg, ether 1. CO2 2H2O CH3 -CH₃ Bromination Grignard reaction