1. Based on the problem description determine the structure of the two compounds designated by a letter as well as the molecule which would form if they reacted (i.e. Determine the structures of A, T and AT).

2. In a short paragraph explain your thinking, and show calculations

Compound CS has a molecular formula C3H120and is made by the reaction of compound C with compound S in the presence of dilute sulphuric acid. 0.5 g of compound C was burned in excess oxygen and 1.22 g CO2 and 0.50 g H2O were produced. Through NMR compound C was shown to have 4 types of hydrogen and no signals between 5.5 and 6.5 ppm. (Hint: remember diastereotopic hydrogens when counting to four.)The IR spectrum showed a broad band at 3330 cm and MS gave a molecular ion peak at 72 m/z. Compound C was achiral and reacted quickly with Lucas reagent. 0.5 g of compound S was burned in excess oxygen and 1.023 g CO2 and 0.314 g H2O were produced. Through NMR compound S was shown to have 4 types of hydrogen with one signal at 12.0 ppm and none between 5.5 and 6.5 ppm. (Hint: remember diastereotopic hydrogens when counting to four.) The IR spectrum showed a very broad band at 3000 cm-and a strong, sharp band at 1711 cm-?. MS gave a molecular ion peak at 86 m/z. Compound S was achiral and showed no reaction with bromine or 2,4-DNP. It did however produce bubbles when reacted with a solution of sodium hydrogen carbonate. Determine the structures of C, S and CS