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study list for exam 1
1. how to draw resonance structures
2. meaning of conjugated vs isolated pi bonds
3. what an orbital is
4. be able to draw MO diagrams for allyl radical and cation and benzene, such as the
one in Fig. 10.2 but you dont need to know how the MOs look, just the relative energy
levels and how to put in the electrons.
5. reaction of allylic halides with nucleophiles to give a mixture of products via the allylic
cation intermediate.
6.free radical bromination of allylic and benzyl positions with NBS
7. colored molecules absorb light and hv = delta E matches the deltaE for the homo
lomo gap.
8. kinetic vs thermodynamic control of reaction of dienes with HBr
8. diels alder reaction products and stereochemistry
9. MO diagram for benzene
10. 4n+2 rule
11. ortho, para, meta nomenclature
12. structure of the aromatic compounds I gave in class including porphyrin ring.
13. benzylic bromination with NBS
14. polymerization of styrene
15. mechanims of electrophilic aromatic substitution.
16. nitration, sulfonation, halogenation, friedel-crafts alkylation/acylation of aromatics
17. how ion exchange resins work
18. activators/deactivators, o/p and m directors
19. how to synthesize disubstituted benzenes using proper strategy to ensure the
correct products (o/p vs m director game).
20. NMR, basic principles of chemical shift (shielding) and basic principles of J coupling.
21. how to sketch an NMR from the structure
22. how to find the structure from the NMR and IR and molecular formula (all 3 will be
given).
23. how to figure out homotopic, heterotopic, enantiotopic and diastereotopic pairs of
protons in a molecule.
24. basic principle of electron impact and electrospray mass spec.
25. mechanism for reaction of alkyl halide with Mg and Li to form organolithiums and
Grignards.
26. reaction of grignard with aldehyde, ketone, CO2 and epoxide.
27. what olefin methathesis is.
28. NaBH4 reduction of aldehydes and ketones including mechanism
29. LiAlH4 reduction of aldehydes and ketones and carboxylic acids
30. Grignard + epoxide to make primary alcohols
31. OsO4 oxidation of alkenes to cis diols.
32. oxidation of alcohols with Jones' reagent. mechanism too.
33. synthesis using grignard/NaBH4, LiAlH4, Jones' reagent like at the end of monday's
lecture.