Procaine is used as an anaesthetic in medicine. It can be synthesised from methylbenzene in five steps as shown in Fig. 7.1. [Figure 7.1 showing synthesis scheme]

1. (a)(i)Name all the functional groups present in procaine.[1]
2. (a)(ii)A molecule of procaine has 13 carbon atoms. State the number of carbon atoms that are sp, sp² and sp³ hybridised in procaine. sp carbons = sp² carbons = sp³ carbons =[1]
3. (b)The proton (¹H) NMR spectrum of procaine dissolved in D₂O is recorded. Predict the number of peaks observed.[1]
4. (c)State why procaine can act as a base.[1]
5. (d)(i)Compound X can be synthesised in two steps from methylbenzene. [Figure 7.2 showing partial synthesis] Draw the structure of compound W in the box provided.[1]
6. (d)(ii)State the reagents and conditions for step 1 and step 2. step 1 step 2[2]
7. (e)Procaine is synthesised in three steps from X. Suggest the reagents and conditions for step 4 and for step 5 in Fig. 7.1. step 4 step 5[3]
8. (f)(i)Explain what is meant by partition coefficient, K_pc.[2]
9. (f)(ii)The partition coefficient of procaine between octan-1-ol and water is 1.77. Octan-1-ol and water are immiscible. A solution containing 0.500 g of procaine in 75.0 cm³ of water is shaken with 50.0 cm³ of octan-1-ol. Calculate the mass of procaine that is extracted into the octan-1-ol. mass of procaine extracted =[2]

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.