The Aromatic Problem

A little problem that the chemists of the 19th century where presented with.

We are travelling back in time to the early 19^th Century, a very exciting time in the world of chemistry. We have carried out a combustion analysis and physical measurements on a clear colourless hydrocarbon isolated from the distillation products of crude oil.

Combustion analysis

Carbon 92.3%

Hydrogen 7.7%

Physical measurements analysis

0.250g of this liquid was vapourised at 100˚C and a pressure of 101.2 kPa. The vapour had a volume of 98cm³. The boiling point was 80˚C and the melting point 5˚C.

Problems

1.                  What can you deduce from the boiling and melting points about the bonding?

2.                  Use the appropriate equation to calculate the Relative molecular mass of this mystery compound.

3.                  Calculate the empirical formula and hence the molecular formula.

Suggest a structure for this compound.

Click here for answers!