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04-BS-12: May 2016

Nivaar worked solution (AI-drafted; not reviewed by a licensed engineer)

  1. Question 1 Structure Elucidation from IR/ 13 C NMR (C 4 H 6 O 2 )
  2. Question 2 Cysteine — pK a Assignment and Ionisation States
  3. Question 3 Two Routes to an Amino Alcohol — Which Succeeds?
  4. Question 4 Doxazosin Synthesis — Reagents and Rationale
  5. Question 5 Solvent Effects on Three Reactions (Hughes–Ingold Rules)
  6. Question 6 Diastereomers of a Trisubstituted Cyclopentane
  7. Question 7 S N 1 or S N 2? Four Cases
  8. Question 8 Chair or Boat — Six Bridged/Caged Systems
  9. Question 9 Position of the Double Bond After Dehydration/Hydrolysis — Enantiopurity
  10. Question 10 Acid-Catalysed α-Bromination of a Ketone
  11. Question 11 Total Synthesis of Proparacaine
  12. Question 12 Why 2-/4-Chloropyridine React with Nucleophiles but 3-Chloropyridine Does Not
  13. Question 13 Proposed Syntheses of Two Amines

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — May 2016. 3 hours, closed-book examination; one aid sheet (8.5×11", both sides) and a Casio or Sharp calculator permitted. Ten questions constitute a complete exam paper (only the first 10 questions as they appear in the answer book are marked, each of equal value) — the source paper in fact prints thirteen questions; all thirteen are answered in full below.

Reference texts: McMurry, Organic Chemistry, 9th ed. (functional-group spectroscopy, amino-acid ionisation, conjugate addition, electrophilic/nucleophilic aromatic substitution, SN1/SN2 and epoxide-opening regiochemistry, stereochemistry and meso compounds, cyclohexane/bridged-ring conformational analysis, α-halogenation, and multi-step synthesis design); Atkins, Physical Chemistry, 11th ed. (Hughes–Ingold solvent-polarity rules).