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REACTIONS STUDIED IN 2601 (* = mechanism included) 1. * Bromination of alkanes and cycloalkanes 2. Addition of hydrogen to an alkene 3.

*Addition of hydrogen halide/CH3COOH to an alkene 4. *Addition of HBr/peroxide to an alkene 5. Addition of H2O/H+ to an alkene 6. *Addition of water to an alkene-oxymercuration 7. *Addition of water to an alkene-hydroboration 8. Addition of alcohol to an alkene-alkoxymercuration 9. *Addition of halogens/CH2Cl2 or CCl4 or CHCl3 to an alkene 10.*Addition of halogens/H2O to an alkene 11. Addition of –OH groups: a) anti hydroxylation b) syn hydroxylation 12. Epoxide formation and ring opening 13. Oxidative Cleavage with hot, conc potassium permanganate 14. Oxidative cleavage with ozone: a) oxidative b) reductive 15. Alkynide anions + primary alkyl halides 16. Alkynide anions + AgNO3(alc) or CuCl(aq) 17. a) Alkynide anions + HCHO b) Alkynide anions + ethylene oxide c) Alkynide anions + aldehyde d) Alkynide anions + ketone 18. Addition of hydrogen to an alkyne: a) complete b) partial, with Lindlar’s catalyst c) partial with sodium, ammonia -17oC 19. Addition of halogens to an alkyne 20. Addition of hydrogen halides to an alkyne 21. Addition of water to an alkyne-oxymercuration 22. Addition of water to an alkyne-hydroboration 23. Oxidation of an alkyne with cold, dilute potassium permanganate 24. Oxidative Cleavage with hot, conc potassium permanganate 25. Oxidative cleavage with ozone

*Alcohol + thionyl chloride 31.26. Review of general chemistry principles and their applications to organic chemistry. alkyl halides. Double dehydrohalogenation of a dihalide 39. optical activity. Absolute and Relative Configurations/R and S Nomenclature. diastereomers. Formation of an alkoxide 35. Reduction of an acid. *Alcohol + HCl/HBr or Lucas reagent 32. Fischer Projections. *Alcohol + PBr3 30. alkynes. stereochemistry of molecules with > 1 chiral Carbons. Oxidation of alcohols: a) complete b) partial 28. . Alcohol dehydration 33. Substitution of an alkyl halide 37. enantiomers. racemic mixtures. *Tosylation of an alcohol 29. Conversion to organometallic reagents a) Gilman’s reagent for chain extension b) Grignard/Organolithium + HCHO c) Grignard/Organolithium + ethylene oxide d) Grignard/Organolithium + aldehyde e) Grignard/Organolithium + ketone f) Grignard/Organolithium + ester g) Grignard/Organolithium + acid chloride h) Grignard/Organolithium + water Nomenclature of alkanes. meso compounds. Esterification of an alcohol 34. alcohols. Elimination (Dehydrohalogenation) of an alkyl halide 38. Williamson’s ether synthesis 36. IR spectroscopy. alkenes. cycloalkanes. aldehyde. Conformations of alkanes and cycloalkanes and their relative stability. Stereochemistry including chirality. or ketone 27.