Compound F has been found in small quantities in some cereals and dried fruit. [Figure 4.1]

1. (a)(i)Give the name of the functional groups labelled A and B. A B[2]
2. (a)(ii)State the number of chiral carbon atoms in one molecule of F.[1]
3. (b)F can be hydrolysed by heating with an excess of dilute hydrochloric acid, as shown. Three products are formed: G and two others. [Figure 4.2] Draw the structures of the other products of the reaction in the boxes provided.[3]
4. (c)(i)State the role of FeCl₃ in this step.[1]
5. (c)(ii)Use the Data Booklet to suggest two reasons why the chlorine atom in compound H substitutes into the ring at the position shown, instead of the other positions in the ring. 1 2[2]
6. (d)(i)Calculate the number of carbon atoms, x, present in J. x =[2]
7. (d)(ii)The mass spectrum has a peak at m/e = 205. Suggest the identity of the fragment lost from J to form this peak.[1]

This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.