1. morphine
codeine
heroin

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

3. R.B. Woodward (1917-1979) 1st modern synthetic organic chemist
Probably greatest organic chemist
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
1st step in the application of quantum mechanics to organic molecules
1981 Nobel Prize in Chemistry (Roald Hoffmann)

4. R.B. Woodward (Early Career)

5. R.B. Woodward (Later Career)

6. R.B. Woodward

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

8. K.C. Nicolaou Taxol Isolated in 1967 from bark of Pacific yew tree
Lung, ovarian, breast, head and neck cancer
11 stereocenters => 211 = 2048 stereoisomers
2 rings & 1 bicyclic ring

9. K.C. Nicolaou Brevotoxin B
Neurotoxin that binds to voltage-gated sodium channels in nerve cells
Naturally found in Karenia brevis which are marine organisms typically found in fish
23 stereocenters => 223 = 8,400,000 stereoisomers
11 trans-fused rings
83 steps, 12 years
91% yield for each step but 0.043% total yield

10. K.C. Nicolaou Maitotoxin Neurotoxin that binds to calcium channels
Naturally produced by Gambierdiscus toxicus which are marine organisms typically found in fish
94 stereocenters => 294 = 1.98 x 1028 stereoisomers
31 trans-fused rings

11. Atomic Orbitals n l ml Orbital Name 1 1s 2 2s -1 2p +1 3 3s 3p -2 3d n1s 2 2s -1 2p +1 3 3s 3p -2 3d n l
Orbital Name 1 1s 2 2s 2p 3 3s 3p 3d

13. Linus Pauling ( )
Probably greatest chemist of the 20th century
Only person too win 2 unshared Nobel Prizes and only person to win 2 unrelated Nobel Prizes
1954 – Chemistry
Peace
“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

14. The Periodic Table and Electronegativity

15. Common Bonding Situations
Hydrogen
1 bond
Carbon
4 bonds (neutral and 8 electrons)
The most common bonding situations that we will encounter for organic compounds are summarized here.
Remember, satisfying the octet rule is most important in determining stability; minimizing formal charges is next.
Hydrogen prefers one bond.
Carbon prefers two bonds.
We will also encounter some less stable carbon species. These are not compounds that can be put in a bottle, but they will appear as reactive intermediates in some chemical reactions.
Reactive Carbon Species

16. 3 bonds and one unshared pair of electrons
Nitrogen
3 bonds and one unshared pair of electrons
Other relatively stable species
Nitrogen prefers three bonds.

17. 2 bonds and 2 unshared electron pairs
Oxygen
2 bonds and 2 unshared electron pairs
Other relatively stable species
Oxygen prefers two bonds.
hydronium ion

18. 1 bond and 3 unshared electron pairs
Halogens
1 bond and 3 unshared electron pairs
also 4 unshared pairs and negative charge
The halogens prefer one bond.

19. Table 2-6a, p. 51

20. Table 2-6b, p. 51

23. These are sigma (s) MOs: symmetrical about the internuclear axis
Here are the two overlapping 1s AOs of the two hydrogen atoms.
In the simplest model, we picture these as either adding or subtracting. If they add, the waves reinforce between the nuclei, resulting in a lower energy, bonding MO.
If they subtract, the waves cancel in the region between the nuclei to give a higher energy, antibonding MO. The place where the AOs cancel is called a node. More nodes means higher energy.
σ MOs are symmetrical about the internuclear axis. Rotation about that axis causes no change in amount of overlap.
These are sigma (s) MOs:
symmetrical about the internuclear axis