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04-BS-12: December 2019

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

  1. Question 1 Cocaine vs. Cocaine Hydrochloride
  2. Question 2 Cholic Acid and Bile Salt Amphiphilicity
  3. Question 3 Benzene Metabolism — Arene Oxide and Phenol
  4. Question 4 Stereochemistry of the Dimethylcyclopropanes
  5. Question 5 Reaction-Energy Diagrams
  6. Question 6 Intermolecular vs. Intramolecular Esterification Equilibrium
  7. Question 7 S N 2 Stereochemistry at a Single Stereocentre
  8. Question 8 Propranolol Total Synthesis
  9. Question 9 Five Syntheses from Cyclohexene
  10. Question 10 Mass Spectrometry, IR, and NMR Structure Elucidation
  11. Question 11 Addition Polymer Monomers
  12. Question 12 Curcumin Tautomerism, Acidity, Colour, and Antioxidant Activity
  13. Question 13 Step-Growth Polymers — Polyesters and Polyamides

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — December 2019. 3 hours, closed-book examination (no calculator; one hand-written aid sheet permitted); NOTES on page 1 state that TEN (10) questions constitute a complete exam paper and only the first 10 as they appear in the answer book are marked, but this sitting prints 13 numbered questions — every question and sub-part below is answered in full.

Reference texts: McMurry, Organic Chemistry, 9th ed. (functional groups, stereochemistry, SN1/SN2 mechanisms and stereochemistry, steroid/bile-acid amphiphilicity, named-drug synthesis design, reaction-energy diagrams, polymer chemistry, arene-oxide metabolism, and mass-spectral/IR/NMR structure elucidation). Every molecular formula, exact mass, and stereochemical (R/S, cis/trans, meso/chiral) assignment below.