An oil with the pleasant odor of lemons, \(\alpha\) -terpinene, has been isolated from the marjoram plant. It has the formula \(\mathrm{C}_{10} \mathrm{H}_{16} .\) Upon ozonolysis, followed by an oxidative workup, it yielded two compounds: oxalic acid and a neutral compound having the formula \(\mathrm{C}_{8} \mathrm{H}_{14} \mathrm{O}_{2}\). When oxidized with sodium hypochloride, the latter was converted to an acidic compound having the formula \(\mathrm{C}_{7} \mathrm{H}_{12} \mathrm{O}_{3}\). This acidic compound was identified as 5 -methyl-4-oxo-hexanoic acid. What is the structure of \(\alpha\) -terpinene?

Based on the given information about α-terpinene (C10H16) and its reaction products, the structure of this compound can be deduced. After undergoing ozonolysis, two compounds are formed, oxalic acid (C2H2O4) and a neutral compound (C8H14O2). The neutral compound, when oxidized with sodium hypochlorite, forms an acidic compound (C7H12O3) identified as 5-methyl-4-oxo-hexanoic acid. The structure of C8H14O2 can be inferred to be 4-Oxopentanal-5-methyl based on the conversion to the acidic compound and its structure. The final structure of α-terpinene can be determined by reconnecting the broken double bond between oxalic acid and 4-oxopentanal-5-methyl, resulting from the ozonolysis reaction. Carbon 1 and Carbon 2 are connected to Carbon 6 and Carbon 5 in 4-oxopentanal-5-methyl, respectively. Hence, the complete structure of α-terpinene would involve a double bond between carbon 1 and carbon 2, and connections between Carbon 6 in 4-oxopentanal-5-methyl to Carbon 1 and Carbon 5 in 4-oxopentanal-5-methyl to Carbon 2.