You have four C5H12O constitutional isomers, identified as A, B, C & D. All of these compounds react with sodium metal to liberate hydrogen gas. On treatment with hot phosphoric acid, each isomer is converted to one or more C5H10 isomers (E, F & G). Each of these three isomers (E, F & G) adds one equivalent of hydrogen (Pt catalyst), producing the same C5H12 compound H. Compounds A, B, C & D each behave differently on treatment with PCC (pyridinium chlorochromate) in methylene chloride. A gives a C5H10O aldehyde M, C gives an isomeric ketone K, D an isomeric aldehyde N, and B fails to react at all. These relationships are all outlined below.
After thinking about these facts and relationships, you should be able to assign structural formulas to all the unknown compounds designated by a bold letter above. To do so select an unknown from the following list and draw a formula using the drawing window on the left below. When you are finished,check your answer by pressing the Check Structure button. A help screen is available for the drawing window.