1.1. This question is about saturated hydrocarbons.

Compound A is shown in Figure 1.

Figure 1

The reaction of compound A with excess fluorine forms compound D, which has a molar mass of 140 g mol⁻¹.

Draw a possible structure for compound D and write the equation for its formation from compound A. Use molecular formulae in the equation.

1.2. The hydrocarbon propane can be reacted with chlorine to prepare 2-chloropropane, CH₃CHClCH₃, by free radical substitution.

i) Write the overall equation and state the conditions for this reaction.

[2]

ii) Outline the mechanism by naming and providing relevant equations for each step in the formation of 2-chloropropane.

[3]

iii) Describe the limitations of this method of preparation.

[2]

1.3. Oxybenzone is a UV light-absorbing chemical which is found in certain sun creams. The structure of oxybenzone is shown in Figure 2 below.

Figure 2

Oxybenzone contains an ether functional group, C-O-C. Identify the other functional groups present in oxybenzone.

1.4. One of the starting molecules used in the synthesis of oxybenzone is shown in Figure 3 below.

Figure 3

Draw the skeletal formula of two other structural isomers of this molecule.