Step 1:

→ To synthesise chloroethane (A) into ethanol (B), is added and heated. is then added and heated.

→ The mixture is then treated with concentrated sulfuric acid and refluxed.

→ Ethanol (B) can be identified using infrared spectroscopy by looking for a broad absorption between 3230 cm ¯¹ and 3550 cm ¯¹, which indicates the presence of an bond. This absorption would not be present in chloroethane (A).

→ Alternative ways to identify ethanol include: mass spectrum analysis (single ion peak at m/z = 46), reactivity tests, and spectrum analysis (3 signals vs 2 for chloroethane).
 

Step 2:

→ Ethanol (B) can be converted into ethanoic acid (C) by combining it with a strong oxidant like sodium carbonate, which produces carbon dioxide bubbles, confirming the presence of a carboxylic acid.

→ Ethanol will not react as above and the compounds can be distinguished.

→ Alternative ways to identify ethanoic acid include: IR or spectrum analysis, litmus indicators, mass spectrum analysis (ion peak at m/z = 60 vs m/z = 46)
 

Step 3

→ Ethyl ethanoate (D) can be synthesised by heating a mixture of ethanol, ethanoic acid and concentrated sulfuric acid under reflux.

→ A spectrum can be used to identify ethyl ethanoate as it will have 3 signals versus ethanol and ethanoic acid that will only have 2 each.

→ Alternative ways to identify ethyl ethanoate include: a distinct smell, no peaks in the IR spectrum or mass spectrum analysis (ion peak at m/z = 102).