Compounds C and D are alkenes with the same molecular formula, C5H10. [Figure 4.1]

1. (a)(i)Give the systematic name of D.[1]
2. (a)(ii)Explain why C and D do not show geometrical (cis/trans) isomerism.[1]
3. (a)(iii)Draw the structure of a molecule that is a positional isomer of C and D.[1]
4. (a)(iv)Give the structural formula of the compound formed when D reacts with H2(g) in the presence of a Pt catalyst.[1]
5. (a)(v)C can form an addition polymer. Draw the structure of one repeat unit of this addition polymer.[1]
6. (b)The mass spectrum of C shows a molecular ion peak at m/e = 70. This peak has a relative intensity of 48.7. The relative intensity of the [M+1] peak is 2.7. Show that this information is consistent with the molecular formula of C.[2]
7. (c)(i)C and D both react with HBr. C reacts with HBr to form E. Complete the diagram in Fig. 4.2 to show the mechanism for this reaction. Draw the structure of the organic intermediate. Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate. [Figure 4.2][3]
8. (c)(ii)D reacts with HBr to produce F, a chiral bromoalkane. Draw the structure of F. [box for F][1]
9. (c)(iii)Explain why the reaction of HBr with C and D produces different major products. [Figure 4.3][2]
10. (d)C can be used to form H. One possible synthesis of H is shown in Fig. 4.5. Different portions of C are used in reactions 1 and 3. Some of the products are then combined to produce H. Fig. 4.5 does not show any of the inorganic products of the reactions. Complete Table 4.1 with the reagents and conditions required for each of the reactions shown in Fig. 4.5. [Figure 4.4] [Figure 4.5] [Table 4.1][3]

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