A gaseous compound used to make both bubble gum and automobile tires was analyzed to determine its properties and toxicity.

(a) When 0.108 g of the compound was analyzed by combustion analysis, 0.352 g of CO₂ and 0.109 g of H₂O were produced.
What is the empirical formula of the compound?

(b) The molar mass of the compound was found to be 54.09 g · mol^–1. What is the molecular formula of the compound?

(c) Draw the structural formulas of at least six possible structural isomers of the compound.

(d) When the compound is exposed to hydrogen gas over a catalyst, the molar mass of the hydrogenated product is 58.12 g · mol^–1. Which of the isomers in part (c) does this information help to eliminate?

(e) A flask of volume 2.45 L was filled with the compound at 25°C and 1.0 atm. Hydrogen bromide gas was pumped into the flask until the total pressure in the flask reached 5.0 atm. Reaction then proceeded to completion because the single product was removed as fast as it was formed. After completion of the reaction, the pressure of the excess HBr in the flask was 2.0 atm. What is the molecular formula of the product?

(f) The product in (e) has three structural isomers, two of which are optical isomers. Draw the structural formulas of the original compound and each of the product isomers. Mark each chiral carbon atom with a star.

(g) Assign a hybridization scheme to each C atom in the original compound.

(h) Write the name of the original compound.