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A-LevelChemistryOrganic synthesis9701/22 · Feb/Mar 2022 · Q415 Marks

Compounds J and K are found in plant oils. [Figure 4.1]

  1. (a)(i)Complete Table 4.1 to state what you would observe when J reacts with the reagents listed. Table 4.1 reagent observation with J 2,4-dinitrophenylhydrazine (2,4-DNPH) Tollens' reagent sodium metal[3]
  2. (a)(ii)J has two optical isomers. Draw the three-dimensional structures of the two optical isomers of J.[2]
  3. (b)(i)K is used to make the addition polymer Perspex®. A synthesis of Perspex® is shown in [Figure 4.2]. Identify L. State the conditions required for reaction 1. L = conditions =[2]
  4. (b)(ii)Draw one repeat unit of the addition polymer Perspex®.[2]
  5. (b)(iii)Use information from Table 4.2 to suggest how the infrared spectra of M and Perspex® would differ. Explain your answer. [Table 4.2][1]
  6. (b)(iv)K can be made from propanone in the three-step synthesis shown in [Figure 4.3]. Complete Table 4.3 to identify the reagent(s) used and the type of reaction in each step. Table 4.3 step reagent(s) type of reaction 1 2 3 Al₂O₃[5]

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Mark scheme

Marking points from the official mark scheme (Feb/Mar 2022). The mark or mark type is shown in brackets.

  1. [1] red / orange / yellow precipitate / ppt / solid
  2. [1] silver mirror / silver / grey solid / precipitate / ppt
  3. [1] effervescence / bubbling / fizzing
  4. [2] [Diagram showing two enantiomers with correct 3D representation of the chiral carbon and four different groups] (Must show wedge and dash bonds for the enantiomers of J)
  5. [1] L = CH₃OH / methanol
  6. [1] conditions = acid(ic) / H⁺ / H₂SO₄ AND (heat under) reflux
  7. [1] carbon backbone with 'dangling' bonds
  8. [1] rest of structure correct
  9. [1] Perspex® would not have absorption 1500–1680 cm⁻¹ AND Perspex® does not have C=C
  10. [1] step 1: KCN / HCN OR NaCN / H₂SO₄
  11. [1] step 1: addition
  12. [1] step 2: H⁺/H₂SO₄(aq)
  13. [1] step 2: hydrolysis / substitution
  14. [1] step 3: elimination / dehydration

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About this question

Topic
Organic synthesis, A-Level Chemistry (syllabus 9701). Structured question, 15 marks.
Source
A-Level Chemistry, Feb/Mar 2022 Paper 2 Variant 2, question 4.

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