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.

A   +   H3PO4 heat E B   +   H3PO4 heat E   +   F C   +   H3PO4 heat F   +   G D   +   H3PO4 heat G		A   +   PCC   methylene chloride M B   +   PCC   methylene chloride No Change C   +   PCC   methylene chloride K D   +   PCC   methylene chloride N
E, F or G  +  H2 & Pt(catalyst)     H

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.