22   7 This question is about the primary alcohol butan‑1‑ol. (a) Which are the intermolecular force(s) between butan‑1‑ol molecules in the liquid phase? (1) A hydrogen bonding only B hydrogen bonding and permanent dipole‑dipole forces only C hydrogen bonding, permanent dipole‑dipole forces and London forces D London forces only (b) The equation for the complete combustion of butan‑1‑ol is shown. CH3CH2CH2CH2OH(l) + 6O2(g) → 4CO2(g) + 5H2O(l) ΔcH d = –2675.6 kJ mol–1 Draw a labelled enthalpy level diagram for this reaction, using the axes provided. You may use the labels ‘reactants’ and ‘products’ in place of the formulae shown in the equation. (2) Enthalpy Progress of reaction Turn over 23   (c) Butan‑1‑ol can be oxidised to produce butanal or butanoic acid. (i) Which is a suitable test and result for butan‑1‑ol? (1) A B C D Test reagent Observation phosphorus(V) chloride PCl5(s) white smoke phosphorus(V) chloride PCl5(s) steamy fumes sodium carbonate Na2CO3(aq) carbon dioxide given off sodium carbonate Na2CO3(aq) effervescence (ii) State how to produce butanal in high yield when butan‑1‑ol reacts with acidified potassium dichromate(VI). (1) .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... (iii) Describe a chemical test, including the expected results, that would confirm the presence of an aldehyde such as butanal. (2) .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... 24   *(iv) Describe, including practical details, how a sample of butanoic acid (boiling temperature 166 °C) could be prepared from butan‑1‑ol (boiling temperature 117 °C) using acidified potassium dichromate(VI). Include labelled diagrams of the apparatus you would use for the reaction, and for collecting the product. You may assume that all necessary safety precautions are observed. (6) .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... Turn over 25   .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... .................................................................................................................................................................................................................................................................................... (Total for Question 7 = 13 marks)