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04-BS-12: December 2016

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

  1. Question 1 Acid/Base Sites in Drug Molecules
  2. Question 2 Pharmacokinetics: Lipophilic vs. Water-Soluble Drugs
  3. Question 3 Differential Amide Reactivity in Penicillin G
  4. Question 4 S N 2 Products and Stereochemistry
  5. Question 5 Two-Step Nucleophilic Synthesis of Propranolol
  6. Question 6 Retrosynthesis of Internal Alkynes via Acetylide Alkylation
  7. Question 7 Multi-Step Synthesis from Acetylene (≤2-Carbon Building Blocks)
  8. Question 8 IR-Spectrum Matching for Six Isomeric/Related C–H, O, and Functional Classes
  9. Question 9 Structure Elucidation: Regiochemistry of Ketone Enolate Alkylation
  10. Question 10 Markovnikov vs. Anti-Markovnikov HBr Addition: Rearrangement vs. Radical Mechanism
  11. Question 11 Multi-Step Aromatic Synthesis Design from Benzene
  12. Question 12 Substituent Effects on Phenol and Carboxylic Acid Acidity
  13. Question 13 Identifying the Four Monomers of a Poly(ester amide) Drug-Delivery Copolymer

Start with Question 1 →

National Exam 04-BS-12, Organic Chemistry — December 2016. 3 hours, closed-book examination (no non-communicating calculator restriction beyond the standard aid sheet, 8.5×11", hand-written both sides). 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. (acid/base theory of drugs, SN1/SN2 stereochemistry, carbocation rearrangements, alkyne synthesis via acetylide alkylation, IR/NMR structure elucidation, electrophilic aromatic substitution and synthesis design, amino-acid pKa); Clayden, Organic Chemistry, 2nd ed. (amide resonance and β-lactam reactivity, radical vs. ionic HBr addition mechanisms); a standard biomaterials reference for the poly(ester amide) drug-delivery polymer chemistry of Question 13 (Katsarava-type AABB poly(ester amide)s built from diacids, diols, and protected diamino acids).