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A-LevelChemistryOrganic synthesis9701/51 · May/June 2019 · Q214 Marks

A student plans to prepare propanone from propan-2-ol and test the product. Reagents provided to the student and some of their hazards are shown in the table. | reagent | hazard | | :---------------------- | :------------ | | propan-2-ol | flammable | | concentrated sulfuric acid | corrosive | | potassium dichromate(VI) | oxidising | | distilled water | non-hazardous |

  1. (a)(i)The full equation for the reaction between propan-2-ol and acidified potassium dichromate(VI) is shown. 3CH₃CH(OH)CH₃ + K₂Cr₂O₇ + 4H₂SO₄ → 3(CH₃)₂CO + K₂SO₄ + Cr₂(SO₄)₃ + 7H₂O Calculate the minimum mass of potassium dichromate(VI) that is needed for complete oxidation of 5.00 g of propan-2-ol to propanone. Give your answer to three significant figures. [Ar: K, 39.1; Cr, 52.0; O, 16.0; C, 12.0; H, 1.0] mass K₂Cr₂O₇ = .............................................. g[2]
  2. (a)(ii)The student is provided with a set of instructions to prepare the propanone. step 1 Add concentrated sulfuric acid to 5.0 g of propan-2-ol in a round-bottomed flask, a few drops at a time. step 2 Dissolve the mass of potassium dichromate(VI) calculated in (a)(i) in a few cm³ of distilled water. step 3 Add this aqueous potassium dichromate(VI) slowly to the mixture in the round-bottomed flask. step 4 Heat the mixture under reflux. step 5 Separate the propanone from the reaction mixture using distillation. The student is also provided with the boiling points of propan-2-ol and propanone. | compound | boiling point/°C | | :---------- | :--------------- | | propan-2-ol | 82.5 | | propanone | 56.5 | Complete the diagram to show how the propanone is separated from the reaction mixture in step 5. Label your diagram fully including the location of propan-2-ol and propanone after distillation has taken place. There is no need to include clamps. [Incomplete distillation apparatus diagram][3]
  3. (a)(iii)The reaction mixture needs heating for reflux to take place. Explain why a water-bath is used to heat the mixture.[1]
  4. (a)(iv)The propanone separated from the mixture in step 5 contains sulfuric acid as an impurity which needs to be removed. Name a reagent that could be added to remove the sulfuric acid and explain how the student would ensure that all of the acid is no longer present. reagent ..................................................... explanation .....................................................[2]
  5. (b)(i)When propanone reacts with a solution of 2,4-DNPH an insoluble compound, X, is produced according to the following equation. [Chemical reaction diagram with structures for 2,4-DNPH, CH₃COCH₃, X, H₂O] The melting point of X can be used to confirm the identity of the carbonyl compound that has reacted with 2,4-DNPH. To do this, solid X must be separated from the mixture. This can be done using method A or method B. [Diagrams of filtration apparatus for Method A and Method B] method A: gravity filtration using a filter funnel, filter paper and a conical flask method B: filtration under reduced pressure using a Buchner funnel and Buchner flask, filter paper and a suction pump to reduce the pressure in the Buchner flask Suggest one major advantage of using method B rather than method A.[1]
  6. (b)(ii)The student places a washed sample of X in a drying oven for an hour. The student records the mass of X. The student wants to ensure that X is completely dry. Describe what the student should do to ensure that X is completely dry.[1]
  7. (b)(iii)5.00 cm³ of propanone reacts with an excess of 2,4-DNPH. The mass of dry X produced is 11.84 g. Calculate the percentage yield of X in this reaction. Mr X = 238 Mr CH₃COCH₃ = 58 density CH₃COCH₃ = 0.789gcm⁻³ percentage yield of X = .............................................. %[3]
  8. (b)(iv)Explain why a 100% yield in the preparation of a pure sample of X is not possible.[1]

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Mark scheme

Marking points from the official mark scheme (May/June 2019). The mark or mark type is shown in brackets.

  1. [1] M1 Mr propan-2-ol is 36 + 16 + 8 = 60 and n propan-2-ol = 5 / 60 = 0.0833(3)
  2. [1] M2 n K2Cr2O7 = 0.0833 / 3 = 0.0278; Mr K2Cr2O7 = 78.2 + 104 + 112 = 294.2; Mass = 294.2 × 0.0278 = 8.16953333 = 8.17 g
  3. [2] (a)(ii) Diagram shows: thermometer in correct position AND condenser showing coolant AND sealed apparatus around round bottomed flask and thermometer with no seal around collection flask (3 points = 2 marks, 2 points = 1 mark)
  4. [1] (a)(ii) Propan-2-ol and propanone in correct locations
  5. [1] Propan-2-ol is flammable AND should not be heated directly / keep away from a naked flame / Bunsen burner
  6. [1] Reagent: sodium carbonate / an alkali
  7. [1] Explanation: carbonate added until no further effervescence / alkali added until indicator shows neutral / not acidic OR use an indicator to test when neutral / for a base/metal - (added until) some solid remains
  8. [1] It is faster / precipitate is drier (a comparison is required)
  9. [1] Return it to the oven for a further period of time / Repeat drying. Reweigh. AND Continue with this process until the mass is constant
  10. [1] M1 Mass of propanone = 5 × 0.789 = 3.945 g only
  11. [1] M2 Mr Propanone = 58
  12. [1] M3 Moles propanone = 3.945/58 = 0.0680; Expected yield = 0.0680 × 238 = 16.184 g (16.18810345); % yield = 11.84 / 16.20 × 100 = 73 % (73.14013058)
  13. [1] The reaction does not go to completion / is reversible / is an equilibrium reaction

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About this question

Topic
Organic synthesis, A-Level Chemistry (syllabus 9701). Structured question, 14 marks.
Source
A-Level Chemistry, May/June 2019 Paper 5 Variant 1, question 2.

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