Question

A neutral liquid compound A, C7H7Br, was insoluble in water and cold concentrated H2SO4. It reacted rapidly with silver nitrate solution to give a pale yellow precipitate. Compound A was reacted with magnesium in anhydrous ether solvent, and to this solution was added compound B, C3H6O, which after treatment with an aqueous acid solution, resulted in the formation of compound C, C10H14O. Compound C did not decolorize a neutral permanganate solution at room temperature, but it did react with sulfuric acid to form as the major product the hydrocarbon, D, C10H12. Ozonolysis of compound D gave compounds E and B. Prominent mass spectrum peaks occured at m/z 77,105 and 106 for compound E and m/z 15,43, and 58 for compound B. SHow the structures of the compounds involved. Explain the mass spectrum peaks. Show the chemical reaction that occured and interpret the results of the chemical tests. ALso explain the significance of any negative test results.

Answer 1