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A-LevelChemistryOrganic synthesis9701/41 · Oct/Nov 2024 · Q715 Marks

A reaction scheme is shown in Fig. 7.1. The reagents needed for reaction 2 and reaction 3 are stated. Reaction 5 takes place when C2H5NH2 is mixed with compound V. No special conditions are required. [Figure 7.1]

  1. (a)Identify compound U which contains only three elements.[1]
  2. (b)Describe the reagents and conditions for reaction 1.[1]
  3. (c)Identify compound V.[1]
  4. (d)Complete the equation for reaction 3. CH3COOH + SOC2 → ______[1]
  5. (e)Identify compound W.[1]
  6. (f)Describe the conditions for reaction 4.[1]
  7. (g)Suggest the reagent needed for reaction 6.[1]
  8. (h)Complete Table 7.1 by adding the reaction numbers, 1, 2, 3, 4, 5 and 6, to the right-hand column. Use the reaction numbers given in Fig. 7.1. Each of the numbers 1, 2, 3, 4, 5 and 6 should be used once only. Table 7.1 type of reaction reaction number(s) hydrolysis addition reduction substitution[4]
  9. (i)Compare the basicities of C2H5NHCOCH3, C2H5NHC2H5 and NH3. Explain your answer. most basic least basic[4]

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Mark scheme

Marking points from the official mark scheme (Oct/Nov 2024). The mark or mark type is shown in brackets.

  1. [1] CH3CN / ethanenitrile
  2. [1] dilute acid / HCl (aq) AND hot / heat (all three components of reagents and conditions required for this mark)
  3. [1] CH3COCl / ethanoyl chloride
  4. [1] CH3COOH + SOCl2 → CH3COCl + HCl + SO2
  5. [1] C2H5Br/C2H5Cl/bromoethane / chloroethane
  6. [1] heat in ethanol AND under pressure / in sealed tube
  7. [1] LiAlH4 / lithium aluminium hydride
  8. [1] hydrolysis: 1
  9. [1] addition: 2
  10. [1] reduction: 2, 6
  11. [1] substitution: 3, 4, 5
  12. [1] Order of basicity: C2H5NHC2H5 (most basic) > NH3 > C2H5NHCOCH3 (least basic)
  13. [1] Basicity is linked to the lone pair/p orbital on N AND its ability to accept/donate a proton/H+
  14. [1] Explanation for C2H5NHC2H5 (amine) being stronger due to +ve inductive effect / electron donating alkyl / R / ethyl group
  15. [1] Explanation for C2H5NHCOCH3 (amide) being weaker because the lone pair/p orbital on N is delocalised into C=O group

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About this question

Topic
Organic synthesis, A-Level Chemistry (syllabus 9701). Structured question, 15 marks.
Source
A-Level Chemistry, Oct/Nov 2024 Paper 4 Variant 1, question 7.

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