M 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.Regio: = regiochemistry; Stereo: = stereochemistry M: = know mechanismDefault is "no carbocation rearrangments" and “no mechanism” unless explicitly stated so.1. HX (tertiary, secondary) Sn1 [4.9+]{Stereo: random. Mechanism} carbocation rearrangementsor PBr3 or SOCl2 [4.13]2. X2, hv {Mechanism} [4.14]3. Acid-cat. Dehydration [5.9]{Regio: Zaitsev; Mechanism} carbocation rearrangements4. E2 elimination [5.15]typically RO-/ROH or KOH/EtOH{Regio: Zaitsev; Stereo: anti; Mechanism }5. H2, catalyst(Pd, Pt, or Ni) [6.1]{Regio: None; Stereo: syn } 6. Hydrogen halide (HCl, HBr, HI) addition to an alkene: [6.4+] {Regio: Markovnikov; Stereo: random; Mechanism } Carbocation Rearrangments! or HBr plus peroxides [6.8]{Regio: anti-Markovnikov; Stereo: random; Mechanism } 7. H2SO4 , Δ {Regio: Markovnikov; Stereo: random. Mechanism} [6.9]8. H2O, Δ [6.9]9. Acid-cat. Hydration [6.10]{Regio: Markovnikov M } carbocation rearrangementsor (1) B2H6, Et2O (2) H2O2, NaOH, H2O [6.12]{Regio: anti-Markovnikov; Stereo: syn; }10. Br2 or Cl2, CH2Cl2 (inert solvent) [6.15]{Regio: None; Stereo: anti; Mechanism} 11. Br2, H2O [6.18]{Regio: OH to more substituted; Stereo: anti; Mechanism}12. RCO3H [6.19]{Stereo: 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]{Regio: None; Stereo: inversion; M(SN2)}limits on RX: Me, primary, un-Β-branched secondary16. R'S-Na+, ROH or DMF or DMSO solvent [Ch.8]{Regio: None; Stereo: inversion; M(SN2)}limits on RX: Me, primary, un-Β-branched secondary17. H2O (solvolysis, SN1) [Ch.8]{Stereo: random; Mechanism} carbocation rearrangements (tertiary, secondary)orHO- (SN2) [Ch.8]{Stereo: inversion M, SN2} methyl, primary, un--branched secondary18.NaN3, DMSO or DMF or ROH solvent (SN2) [Ch.8]{Stereo: inversion; Mechanism} limits on RX: Me, primary, un--branched secondary19.NaX, DMSO or DMF or ROH solvent (SN2) [Ch.8]{Stereo: inversion; Mechanism} limits on RX: Me, primary, un--branched secondary20. NaCN, DMSO (or ROH solvent) {Mechanism; Stereo: invert} [Ch. 8]21. R’O- in R’OH or DMSO (R=good SN2)or R’OH solvent (R good Sn1)22. (1) Na (2) R’X (R’=good SN2) or H2SO4/R’OH solvent (R=R’)23. TsCl, pyridine [8.12]24. KOH/EtOH or RONa/ROH {E2 Mechanism} [Ch.8, also 5.15]25. KOH/EtOH or RONa/ROH {E2 Mechanism} [Ch.8, also 5.15]26. 2 (or 3) NaNH2, NH3 {E2 mechanism} [9.7]27. H2, catalyst(Pd, Pt, or Ni) {Regio: None; Stereo:syn} [9.9]28. HX {Regio: Markovnikov; Stereo:mixed ; Mechanism} [9.11]29. H2, Lindlar's catalyst(Pd, Pb(OAc)2, quinoline {Regio: None; Stereo: syn } [9.9] orNa, NH3 {Regio: None; Stereo: anti } [9.10]30. xs HX {Regio: Markovnikov; Stereo:mixed; Mechanism} [9.11]31. excess HX {Regio: Markovnikov; Mechanism} [9.11]32. H2O, H2SO4, HgSO4 [9.12]{Stereo: Markovnikov; terminal alkynes give methyl ketones. Mechanims: enol to keto tautomerization}33. Br2, CH2Cl2 (inert solvent) {Regio: None; Stereo: anti} 9.13]34. excess Br2, CH2Cl2 (inert solvent) {Regio: None; Stereo: anti} [9.13] 35. (1) O3, CH2Cl2, -78ºC (2) H2O