READ THIS FIRST:What here's is *NOT* everything you need to know about these reactions. This is only a bare-bones outline of reagents and a few pertinent facts. You need to not only have this information in your head, but be able to use all this in solving real problems. Don't think that just memorizing this list will result in a C grade. This is the framework for organizing the knowledge in your head, so that you can pull up the right facts when needed.R: = regiochemistry; S: = stereochemistry M: = know mechanismDefault is "no carbocation rearrangments" and “no mechanism” unless explicitly stated so.1. HX (tertiary, secondary) SN1/SN2 [4.9+]{ M; S: random} carbocation rearrangementsor PBr3 or SOCl2 [4.14]2. X2, hv {M} [4.15]3. Acid-cat. Dehydration [5.9]{R: Zaitsev; M} carbocation rearrangements4. E2 elimination [5.14] typically RO-/ROH or KOH/EtOH{R: Zaitsev; S: anti; M } or E1 [5.18]5. H2, catalyst(Pd, Pt, or Ni) [6.1]{R: None; S: syn } 6. Hydrogen halide (HCl, HBr, HI) addition to an alkene: [6.4+] {R: Markovnikov; S: random; M } Carbocation Rearrangments! or HBr plus peroxides [6.18]{R: anti-Markovnikov; S: random; M } 7. H2SO4 , Δ {M; R: Mark; S: random} [6.8]8. H2O, Δ [6.8]9. Acid-cat. Hydration [6.9]{R: Markovnikov M } carbocation rearrangementsor (1) B2H6, Et2O (2) H2O2, NaOH, H2O [6.11]{R: anti-Markovnikov; S: syn; }10. Br2 or Cl2, CH2Cl2 (inert solvent) [6.14]{R: None; S: anti; M} 11. Br2, H2O [6.17]{R: OH to more substituted; S: anti; M}12. RCO3H [6.19]{S: syn, with retention at alkene E/Z }13. (1) O3, CH2Cl2, -78ºC (2) Me2S or Zn [6.20]14. (1) O3, CH2Cl2, -78ºC (2) H2O [6.20]15. HS-Na+, ROH or DMF or DMSO solvent [Ch.8]{R: None; S: inversion; M(SN2)}limits on RX: Me, primary, un-Β-branched secondary16. R'S-Na+, ROH or DMF or DMSO solvent [Ch.8]{R: None; S: inversion; M(SN2)}limits on RX: Me, primary, un-Β-branched secondary17. H2O (solvolysis, SN1) [Ch.8]{S: random; M} carbocation rearrangementstertiary, secondaryorH2O, H2SO4, heat (SN2) [Ch.8]{S: inversion M, SN2} methyl, primary, un--branched secondary18.NaX, DMSO or DMF or ROH solvent (SN2) [Ch.8]{S: inversion; M} limits on RX: Me, primary, un- -branched secondary19. NaCN, DMSO (or ROH solvent) {M; S: invert} [Ch. 8]20. TsCl, pyridine [8.12]21. KOH/EtOH or NaOR/ROH {E2 mechanism} [Ch.8, also 5.14]22. 2 NaNH2, NH3 {E2 mech} [9.7]23. H2, catalyst(Pd, Pt, or Ni) {R: None; S:syn} [9.9]24. H2, Lindlar's catalyst(Pd, Pb(OAc)2, quinoline {R: None; S: syn } [9.9] orNa, NH3 {R: None; S: anti } [9.10]25. HX {R: Mark; S:mixed } [9.11]26. HX {R: Mark; S:mixed} [9.11]27. excess HX {R: Markovnikov} [9.11]28. H2O, H2SO4, HgSO4 [9.12]{S: Markovnikov; terminal alkynes give methyl ketones. M: enol to keto tautomerization}29. Br2, CH2Cl2 (inert solvent) {R: None; S: anti} 9.13]30. excess Br2, CH2Cl2 (inert solvent) {R: None; S: anti; M} [9.13] 31. (1) O3, CH2Cl2, -78ºC (2) H2O [9.14]32. H2NNH2, KOH, triglyme, Δ (Wolff-Kishner) or Zn/HCl (Clemmensen): [12.8]33. Mg, Et2O (or THF) {S: race} [14.4]34. H2O (or any protic compound) [14.5]35. (1) LiAlH4, Et2O (2) H2O or NaBH4, MeOH [15.2]36. (1) LiAlH4, Et2O (2) H2O [15.3]37. (1) RMgBr (2) H3O+ [15.4]38. OsO4(cat), tBuOOH, tBuOH, HO- {S: syn} [15.4]39. H2SO4 (Cat. SN1) with 2 ROH {M; rear} [15.7]40. R’OH, H2SO4 (Fischer esterification) {M} [15.8]41. a. (2º ROH to ketone): Na2Cr2O7, H2SO4, H2O or CrO3, H2SO4, H2O [15.9] b. (1º ROH to aldehyde): CrO3, pyridine, HCl [15.9]42. (1º ROH to acid) Na2Cr2O7, H2SO4, H2O or CrO3, H2SO4, H2O [15.9]43. HIO4 [15.11]44. R’O-, R’OH (Williamson ether syn) {M; S: inversion at RX} [16.6]45. HX, Δ {M; S: yes; R: yes} [16.8]46. HO-, H2O {M; R: yes; S: anti} [16.10]47. HO-, H2O or H2SO4, H2O {M; S: anti} [16.12-.13]48. RO-, ROH or ROH, H2SO4 {M; S: anti} [16.12-.13]49. HX {M; R: yes; S: yes} [16.13]50. (1) LiAlH4, Et2O (2) H2O {R: yes; S: yes}