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04-BS-12: December 2018

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

  1. Question 1 Acid–Base Sites in Ibuprofen and Cocaine
  2. Question 2 S N 1 vs. S N 2 — Four Substitution Reactions
  3. Question 3 Two Routes to Each Ether
  4. Question 4 Stereochemistry of Substitution Products
  5. Question 5 Cholic Acid → Bile Salt Amphiphilicity
  6. Question 6 Propranolol Synthesis
  7. Question 7 Melting Points of Elaidic, Oleic, and Stearic Acids
  8. Question 8 Reagents for the Cyclopentene Reaction Web
  9. Question 9 The Ascorbate (Vitamin C) Radical
  10. Question 10 Diels–Alder Products and Stereochemistry
  11. Question 11 Brevicomin — Structure and Synthesis
  12. Question 12 Arene Oxide Metabolism
  13. Question 13 Mass Spectrometry, IR, and NMR Structure Elucidation

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — December 2018. 3 hours, closed-book examination (one Casio/Sharp-approved calculator and 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. (Brønsted acid–base sites in drugs, SN1/SN2 mechanism selection, Williamson ether synthesis, SN2 stereochemistry at a stereocentre, steroid/bile-acid amphiphilicity, named-drug synthesis design, fatty-acid melting-point trends, epoxide/alkene interconversion chemistry, radical stability and antioxidants, Diels–Alder stereochemistry, bicyclic-ketal pheromone synthesis, arene-oxide metabolism, and mass-spectral/IR/NMR structure elucidation). Every molecular formula, exact mass, and stereochemical (R/S, cis/trans) assignment below.