Fig. 4.1 shows some reactions of compound D, 2-bromobutane. [Fig. 4.1]

1. (a)(i)State the reagent and conditions used to form E in reaction 1.[1]
2. (a)(ii)Draw the structure of one repeat unit of the addition polymer that forms from E.[1]
3. (a)(iii)E also forms when F is heated strongly in the presence of an Al2O3 catalyst. Write an equation for this reaction.[1]
4. (b)(i)Predict what is observed in reaction 2.[1]
5. (b)(ii)Identify the yellow precipitate and the organic ion formed in reaction 3. yellow precipitate organic ion[2]
6. (c)(i)State the type of reaction that occurs in reaction 4.[1]
7. (c)(ii)Reaction 5 is similar to the reaction of LiAlH₄ with carboxylic acids to form alcohols. Suggest the role of LiAlH4 in reaction 5.[1]
8. (d)(i)Fig. 4.2 shows the infrared spectrum of one of the compounds D, E, F, G or H. Use information from Table 4.1 (on page 14) to identify which of the compounds D, E, F, G or H produces the infrared spectrum in Fig. 4.2. Explain your answer.[2]
9. (d)(ii)In the mass spectrum of D, the relative abundance of the molecular ion peak is 3.4. Predict the relative abundance of the M+2 peak for D. Explain your answer.[1]

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