The three substances shown all have some acidic properties. [Figures of propanoic acid, propan-1-ol, phenol]

1. (a)Write an equation for the reaction between propan-1-ol and sodium metal.[1]
2. (b)(i)Give the order of the relative acidities of propanoic acid, propan-1-ol and phenol, stating the most acidic first.[1]
3. (b)(ii)Explain your answer to (i).[2]
4. (c)Methanoic acid, HCO₂H, has a similar acid strength to propanoic acid. Describe a chemical test to distinguish between these two acids. Name the acid which gives a positive result in this test and describe the observations that would be made.[2]
5. (d)The ester phenyl propanoate, C2H5CO2C6H5, can be made from phenol and propanoic acid in a two-step synthesis. The first step produces an acyl chloride. For this two-step synthesis, draw the structure of the product of the first step, state the reagents and conditions needed for each step of the synthesis.[3]
6. (e)(i)An unknown compound, Z, is propan-1-ol, propanal or propanoic acid. The proton NMR spectrum of Z dissolved in CDCl3 is shown. [Figure of NMR spectrum] From the proton NMR spectrum, identify Z.[1]
7. (e)(ii)State one feature that would be seen, and why, in the proton NMR spectra of each of the two compounds that are not Z.[2]

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