Some reactions of compound G are shown. [Figure 4_G_scheme]

1. (a)(i)State the type of reaction that occurs in reaction 1.[1]
2. (a)(ii)Suggest the reagent(s) and conditions required for reaction 1.[2]
3. (a)(iii)Draw the structure of the organic product, H, from reaction 2.[1]
4. (a)(iv)State what you would observe in reaction 3.[1]
5. (a)(v)Give the type of reaction shown by reaction 4.[1]
6. (b)G and J are structural isomers of each other. [Figure 4b_G_J_structures]
7. (b)(i)Name the type of structural isomerism shown by G and J.[1]
8. (b)(ii)Suggest one chemical test that can distinguish G from J. Give the result of the test with each compound.[2]
9. (b)(iii)State the role of NaBH4 in the reactions with G and J. [Figure 4b_K_scheme][1]
10. (b)(iv)Identify the organic product K.[1]
11. (c)P and Q have the same molecular formula as G. [Figure 4c_P_Q_structures] Complete the table with the expected observations for the reactions of P and Q with the named reagents. [Table with 'reagent', 'result with P', 'result with Q'][3]
12. (d)The structure of compound L is shown. R represents a hydrocarbon chain. [Figure 4d_L_structure] A student was asked to deduce the full structure of L. The student analysed L using infrared spectroscopy. The following spectrum was obtained. [Figure 4d_IR_spectrum] Absorption Y shows that L has a C=C bond present in the R group. The student decided to treat L with hot concentrated acidified potassium manganate(VII). The products of the reaction are shown. [Figure 4d_L_oxidation_scheme]
13. (d)(i)Identify the bonds responsible for the absorptions marked X and Z.[1]
14. (d)(ii)Name M.[1]
15. (d)(iii)Use the information in (d) to deduce the molecular formula of L.[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.