morphinecodeineheroin

Ibuprofen R form non-active side effects S form active anti-inflammatory

R.B. Woodward ( ) 1965 Nobel Prize in Chemistry “outstanding achievements in the art of organic synthesis Also made VERY important observations in the development of the Woodward-Hoffman rules of ring closure 1 st step in the application of quantum mechanics to organic molecules 1981 Nobel Prize in Chemistry (Roald Hoffmann) 1 st modern synthetic organic chemist Probably greatest organic chemist

R.B. Woodward (Early Career)

R.B. Woodward (Later Career)

R.B. Woodward

K.C. Nicolaou Penn ( ) Scripps Research Institute and UC-San Diego (1989-present) Modern day R.B. Woodward

K.C. Nicolaou Taxol 11 stereocenters => 2 11 = 2048 stereoisomers 2 rings & 1 bicyclic ring Isolated in 1967 from bark of Pacific yew tree Lung, ovarian, breast, head and neck cancer

K.C. Nicolaou Brevotoxin B 23 stereocenters => 2 23 = 8,400,000 stereoisomers 11 trans-fused rings 83 steps, 12 years 91% yield for each step but 0.043% total yield Neurotoxin that binds to voltage-gated sodium channels in nerve cells Naturally found in Karenia brevis which are marine organisms typically found in fish

K.C. Nicolaou Maitotoxin 94 stereocenters => 2 94 = 1.98 x stereoisomers 31 trans-fused rings Neurotoxin that binds to calcium channels Naturally produced by Gambierdiscus toxicus which are marine organisms typically found in fish

Atomic Orbitals nlOrbital Name 101s 202s 212p 303s 313p 323d nlmlml Orbital Name 1001s 2002s 21 2p s 31 3p d 0 1 2

Linus Pauling ( ) “The Nature of the Chemical Bond” Protein Structure Antibody Structure and Process Molecular cause of Sickle-cell anemia Electronegativity Resonance Vitamin C and the Common Cold Probably greatest chemist of the 20 th century Only person too win 2 unshared Nobel Prizes and only person to win 2 unrelated Nobel Prizes 1954 – Chemistry Peace

The Periodic Table and Electronegativity

Common Bonding Situations Hydrogen1 bond Carbon4 bonds (neutral and 8 electrons) Reactive Carbon Species

Nitrogen3 bonds and one unshared pair of electrons Other relatively stable species

Oxygen2 bonds and 2 unshared electron pairs Other relatively stable species hydronium ion

Halogens1 bond and 3 unshared electron pairs also 4 unshared pairs and negative charge

Table 2-6a, p. 51

Table 2-6b, p. 51