question_answer

A conjugated alkadiene having molecular formula \[{{C}_{13}}{{H}_{22}}\] on ozonolysis yielded ethyl methyl ketone and cyclohexanecarbaldehyde. Identify the diene, write its structural formula and give its IUPAC name.

Answer:

                The structures of the products of ozonolysis are:                 Since, the total number of carbon atoms of the two products is 11 (4 + 7) while the MF of the conjugated diene is \[{{C}_{13}}{{H}_{22}},\] therefore, the ozonolysis must have also produced another two carbon product. Further since the given compound \[({{C}_{13}}{{H}_{22}})\] is an alkadiene, therefore, this two carbon product must be glyoxal, \[O=CH-CH=O\]. Replace the oxygen atoms from these three products by double bonds, the structure of the alkadiene is