Students will learn
(1) syntheses and reactions of alkenes
(2) syntheses and reactions of alkynes
(3) structures and reactions of benzene and its derivatives
so that they will learn similarities and dissimilarity in the structures and reactivities of those organic compounds involving carbon-carbon unsaturated bonds.
According to the Curriculum Policy of the Department, the series of Organic Chemistry course will cover basics on organic material science. This course focuses on the chemistry of carbon-carbon unsaturated compounds as mentioned above. Those who will take this class are required to understand the contents learned in Organic Chemistry I, and are strongly recommended to take Stereochemistry in order to understand structures and reactivities comprehensively.
This course will cover electrophilic addition reaction to alkene and alkynes, electrophilic substitution reaction of benzene derivatives, in addition to aromaticity and electrocyclic reactions that will be discussed on the basis of molecular orbital. Nomenclature and spectroscpy are out of the scope of this class.
2. Structure and stability of alkenes (Chapter 11-5)
Synthesis of alkenes: E1 and E2 elimination, Saytzeff’s rule, Hofmann’s rule (11-6 to 11-7)
3. Reactivity of alkenes (1): Hydrogenation, electrophilic addition, Markovnikov’s rule, addition of hydrogen halogenide and halogen (12-2 to 12-5)
4. Reactivity of alkenes (2): Generality of nucleophilic addition, hydrogenation (oxymercuration-demercuration and hydroboration-oxydation), addition of carbene and carbenoid (12-6 to 12-9)
5. Reactivity of alkenes (3): epoxydation, dihydroxylation, ozonolysis, (12-10 to 12-12)
6. Alkynes: Structure, synthesis, reduction, nucleophilic addition (13)
7. Delocalized pi-electron system (1): Halogenation and nucleophilic substitution of allylic compounds. Kinetic and thermodynamic controls in the addition to dienes. （14−1, 14-3 to 14−7）
8. Delocalized pi-electron system (2): Cycloaddition, electrocyclization, sigmatropic rearrangement, molecular orbital （14−8 to 14−10）
Radical reactions (12-13 and 14-2)
9. Benzene and aromaticity: Structure, resonance energy, Huckel’s rule （15−1 to 15−7）
10. Reactivity of benzenes (1): Aromatic electrophilic substitution, nitration, sulfonylation, alkylation, acylation （15−8 to 15−13）
11. Reactivity of benzenes (2): Orientation of aromatic electrophilic substitution （16−1 to 16−4）
12. Reactivity of benzenes (3): synthesis of substituted benzenes, polycyclic aromatic hydrocarbons （16−5 to 16−7）
13. Reactivity of benzene derivatives (1): alkylbenzenes, reactions at benzylic positions, electrophilic substitution of phenols （22−1 to 22−3, 22−5, 22−6）
14. Reactivity of benzene derivatives (2): Aromatic nucleophilic substitution, benzynes, electrocyclic reactions, diazonium salts, diazo coupling reactions （22−4, 22−7 to 22−11）
In advance to every class, students are supposed to read the textbook and summarize the points in a notebook. At the beginning of every class, quiz will be held at the beginning of every class and notebooks will be checked. In the classes, discussions and excises will be conducted.
Quiz (40%) and final exam (60%)
K. Peter C. Vollhardt, Neil E. Schore,Organic Chemistry: Structure and Function,7th Edition,W. H. Freeman,2014