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04-BS-12: December 2017

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

  1. Question 1 Bronsted–Lowry Acidity/Basicity of Drug Molecules
  2. Question 2 Pharmacokinetics — THC vs. Ethanol Detection Windows
  3. Question 3 Penicillin G — Differential Amide Reactivity
  4. Question 4 S N 2 Reactions — Products and Stereochemistry
  5. Question 5 Stepwise Synthesis of Propranolol
  6. Question 6 Retrosynthesis — Acetylide + Alkyl Halide
  7. Question 7 Synthesis from Acetylene (≤C 2 Fragments)
  8. Question 8 IR Spectrum Matching
  9. Question 9 Structure Elucidation from MS/IR/NMR
  10. Question 10 Markovnikov vs. Anti-Markovnikov HBr Addition
  11. Question 11 Synthesis from Benzene (Seven Targets)
  12. Question 12 Explaining Relative Acidities (pK a )
  13. Question 13 Poly(ester amide) Monomer Identification

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — December 2017. 3 hours, closed-book examination (no calculator required); 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. (acid–base strength of drugs, pharmacokinetics/lipophilicity, β-lactam reactivity, SN2 stereochemistry, Williamson-ether-type syntheses, alkyne alkylation, IR/NMR structure elucidation, radical vs. ionic HBr addition, electrophilic aromatic substitution & synthesis design, acid strength/resonance & induction, polymer/monomer identification). Every molecular formula, mass balance, and stereochemical (R/S) assignment below.