Organochlorine compounds can undergo hydrolysis. R-Cl + H₂O → R−OH + HCl

1. (a)State and explain the relative rates of hydrolysis of the following compounds. CH3CH2Cl CH3COCl C6H5Cl[3]
2. (b)(i)Epibatidine is a naturally occurring organochlorine compound. [Figure 9.b] State what is meant by the term weak base.[1]
3. (b)(ii)A molecule of epibatidine contains two nitrogen atoms, both of which can act as a base. Epibatidine reacts with HCl(aq). Complete the structure to suggest the product formed in this reaction. [Figure 9.b.ii][1]
4. (c)(i)Polyamides, such as nylon-6, can be prepared from a monomer that contains both an amine and an acyl chloride functional group. [Figure 9.c] When the nylon-6 monomer is hydrolysed, bonds are broken and formed. By considering the two steps in the mechanism of the reaction, complete the table by placing one tick (✔) in each row to indicate the types of bonds broken and formed during the mechanism. [Table 9.c.i: bonds broken | σ bonds only | π bonds only | both σ and π bonds bonds formed | σ bonds only | π bonds only | both σ and π bonds][1]
5. (c)(ii)Draw two repeat units of nylon-6. The amide bond should be shown fully displayed.[2]
6. (d)An addition polymer made from two different alkene monomers is called a co-polymer. A section of a polyalkene co-polymer is shown. [Figure 9.d] Draw the structure of the two alkene monomers which produce this co-polymer.[2]
7. (e)Explain why polyamides normally biodegrade more readily than polyalkenes.[1]
8. (f)(i)The alkene phenylethene can be prepared from benzene in three steps. [Figure 9.f] Deduce the identity of compound H and draw its structure in the box.[1]
9. (f)(ii)Suggest reagents and conditions for each of the steps 1–3. step 1 step 2 step 3[3]

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