Question

hallenge Problem: This question is designed to be challenging. It presents information in an unfamiliar way. It is meant to make you think and is good practice for how you take a word problem and set it up in a way that is easier to see what is going on. Using Talking to the Text"', think about how to rewrite the information in an easier format (it is a reaction). When you are given information ask yourself, what does that mean? What can I conclude from that information? Is it relevant? Unknown Q is determined to have a molecular formula of CoH120. Q is not optically active, and passing it through a chiral column does not separate it into enantiomers. Qdoes not react with Br2 nor does it take up H2 under catalytic hydrogenation. Heating of Q with H2S04 gives product R, which can be separated into enantiomers. ketoaldehyde of formula CsH1002. Propose structures for Q, R and S and write out a reaction scheme showing the conversion of Q through to s. Ozonolysis of a single enantiomer of R produces S an acyclic, optically active

Answer 1

Q molecular formula show one degree of unsaturation. But no reaction with H2 and Br2 shows Q is cyclic alcohol.