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39 questions · 15 almanac · 0 findings

Organic Synthesis

Methods for constructing organic molecules.

Connects to Drug Discovery and Pharmacology8 Physical Chemistry5 Infectious Disease4 Organic Chemistry4 Catalysis3 Vitamins and Nutrition Science3 Nobel Prize History2 Algorithms and Data Structures1 Click and Bioorthogonal Chemistry1 History of Chemistry1 History of Science and Scientists1 Isotopes and Isotope Techniques1
Almanac Building Blood, Atom by Atom
  • What structural features make haemin a chemically difficult molecule to synthesize?
  • Why was Fischer's total synthesis of haemin considered a proof of concept for organic chemistry?
  • What later syntheses, like vitamin B12 or penicillin, followed the same identify-then-build logic as Fischer's haemin work?
Almanac Two Molecules, One Ring, No Waste
  • What makes the Diels-Alder reaction between a diene and a dienophile so efficient compared to other synthesis routes?
  • Why did it take until 1950 for the Nobel committee to recognize a reaction published in 1928?
  • Which modern pharmaceuticals and natural products rely on the Diels-Alder reaction?
Almanac Molecules Built Like Blueprints, Not Guesses
  • How did organic synthesis typically proceed before Woodward's methods, and what made his approach different?
  • Which complex natural molecules did Woodward succeed in synthesizing over his career, and why was each considered difficult?
  • What are the Woodward-Hoffmann rules, and how did the vitamin B12 collaboration with Roald Hoffmann produce them?
  • How does the pharmaceutical industry's modern ability to manufacture complex molecules trace back to Woodward's methods?
Almanac Your Hands Are Not the Same
  • How did John Cornforth use isotopically labelled hydrogen to trace enzyme reactions despite being deaf?
  • What is the R/S notation Vladimir Prelog developed, and why did chemists need it?
Almanac Placing One Atom Exactly Where You Want It
  • What problem does Brown's hydroboration reaction solve in organic synthesis?
  • How does the Wittig reaction convert a carbonyl group into an alkene?
  • Why do these two reactions matter so much for pharmaceutical manufacturing?
Almanac A Map of Which Roads Are Closed
  • What are frontier molecular orbitals and why do they govern a molecule's reactivity?
  • How does the symmetry of electron wavefunctions determine whether a reaction is allowed or forbidden?
  • Why was R. B. Woodward not included in the 1981 Chemistry prize despite co-developing the rules?
  • How did the Woodward-Hoffmann rules change how synthetic chemists plan new reactions?
Almanac Working Backward From the Molecule
  • What is retrosynthetic analysis, and how does it reverse the usual question asked in organic synthesis?
  • How did organic synthesis work before Corey's framework, and why was it hard to teach?
  • How many total syntheses of natural products did Corey complete using his method, and why does that matter for the pharmaceutical industry?
Almanac A Ghost Held Still Long Enough to Study
  • Why were carbocations so hard to study before Olah's work, given how common they are in industrial chemistry?
  • How do superacids stop a carbocation from reacting away, and why does that let chemists examine it with NMR?
  • What are non-classical, bridged carbocation structures, and why did they provoke controversy among chemists?
  • What industrial processes, like oil cracking or fuel refining, depend on understanding carbocation chemistry?
Almanac Teaching Molecules Left From Right
  • How did William Knowles use a chiral catalyst to make a purer version of the Parkinson's drug L-DOPA?
  • What problem in drug manufacturing did asymmetric catalysis solve for the pharmaceutical industry?
Almanac Two Pairs of Dancers Swap Partners
  • What happens chemically during olefin metathesis, and why was the mechanism puzzling for decades?
  • Why were the original metathesis catalysts unsuitable for pharmaceutical chemistry, and how did Grubbs and Schrock fix that?
Almanac A Carpenter's Plane for Carbon Atoms
  • Why was it so difficult to bond carbon atoms together predictably before palladium catalysis?
  • What role does palladium play in Heck, Negishi, and Suzuki coupling reactions?
Almanac A Third Way to Build a Molecule
  • What are the drawbacks of metal catalysts and enzymes that organocatalysis avoids?
  • How did Benjamin List use the amino acid proline as a catalyst?
  • Why did List and MacMillan arrive at the same discovery independently in 2000?
  • How does organocatalysis make pharmaceutical manufacturing cleaner and cheaper?