A-LevelChemistryOrganic synthesis9701/42 · Oct/Nov 2021 · Q910 Marks
Butylamine, CH₃CH₂CH₂CH₂NH₂, can be synthesised from different organic compounds by using suitable reagents. Each reaction involves one step.
- (a)Complete the table to describe three different syntheses. • One of the three syntheses should involve a nucleophilic substitution reaction. • The starting organic compound for each synthesis should contain a different functional group. • A different reagent should be used for each synthesis. starting organic compound reagent and conditions[6]
- (b)Compare and explain the relative basicities of ammonia, butylamine and phenylamine.[4]
Mark scheme
Marking points from the official mark scheme (Oct/Nov 2021). The mark or mark type is shown in brackets.
- [1] 1-butyl halide, e.g. CH₃CH₂CH₂CH₂Br
- [1] NH₃ under pressure or heated in sealed tube
- [1] butanenitrile CH₃CH₂CH₂CN
- [1] H₂ and Ni or Pt / LiAlH₄ / Na + ethanol
- [1] butanamide CH₃CH₂CH₂CONH₂
- [1] LiAlH₄ / Na + ethanol
- M1 butylamine > ammonia > phenylamine [1]
- M2 basicity related to ability of Ip to accept proton / H⁺ [1]
- M3 butylamine is stronger because of positive inductive effect of alkyl group / C₄H₉ [1]
- M4 phenylamine is weaker because Ip on N is delocalised into ring [1]
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