Organic Analytical Techniques (Edexcel International A Level Chemistry)

A compound Q contains the elements carbon, hydrogen and oxygen only.

Combustion analysis of 4.91 g of Q produces 14.6 g of carbon dioxide and 3.58 g of water.

Show that the molecular formula of Q is C₁₀H₁₂O.

You must show all your working.

[M_r of Q = 148]

The high resolution proton NMR spectrum of Q is shown.

Deduce the structure of Q. Justify your answer by considering the relative peak areas, the chemical shifts and the splitting patterns.

You will find it helpful to refer to page 8 of the Data Booklet.

The peak at 3.6 ppm is due to a proton environment on a carbon bonded to the benzene ring. The peak is not where it might be expected from the general values in the Data Booklet.