(a) Explain why amides are much weaker bases than amines. [2] (b) Fig. 9.1 shows the preparation of 2-phenylethylamine, C6H5CH2CH2NH2, by three different routes. [Figure 9.1] (i) Suggest structures for compounds M and N and draw them in the boxes in Fig. 9.1. [2] (ii) Give the reagents and conditions for reaction 1. [1] (c) Fig. 9.2 shows compound H which is a useful starting material in organic synthesis. [Figure 9.2] Η contains an alkene and an amine functional group. Name the other functional group and give the classification of the amine group in H. other functional group in H classification of amine [1] (d) Ozonolysis involves the oxidative cleavage of a C=C bond in alkenes using ozone, O3, as shown in Fig. 9.3. [Figure 9.3] Fig. 9.4 shows the first step in this reaction which involves the formation of an ozonide intermediate. [Figure 9.4] (i) On Fig. 9.4, draw three curly arrows to complete the mechanism of this step. [2] (ii) L is formed from alkene K, C8H14, by a similar reaction to that shown in Fig. 9.3. [Figure L] Suggest the structure of K. [drawing box] [1]

1. (a)Explain why amides are much weaker bases than amines.[2]
2. (b)(i)Suggest structures for compounds M and N and draw them in the boxes in Fig. 9.1.[2]
3. (b)(ii)Give the reagents and conditions for reaction 1.[1]
4. (c)Η contains an alkene and an amine functional group. Name the other functional group and give the classification of the amine group in H. other functional group in H classification of amine[1]
5. (d)(i)On Fig. 9.4, draw three curly arrows to complete the mechanism of this step.[2]
6. (d)(ii)L is formed from alkene K, C8H14, by a similar reaction to that shown in Fig. 9.3. [Figure L] Suggest the structure of K. [drawing box][1]

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