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 mechanism
Default is "no carbocation rearrangments" and “no mechanism” unless explicitly stated so.
1. HX (tertiary, secondary) Sn1 [4.9+]
{ M; S: random} carbocation rearrangements
or PBr3 or SOCl2 [4.13]
2. X2, hv {M} [4.14]
3. Acid-cat. Dehydration [5.9]
{R: Zaitsev; M} carbocation rearrangements
4. E2 elimination [5.15]
typically RO-/ROH or KOH/EtOH{R: Zaitsev; S: anti; M }
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!
HBr plus peroxides [6.8]
{R: anti-Markovnikov; S: random; M }
7. H2SO4 , Δ {M; R: Mark; S: random} [6.9]
8. H2O, Δ [6.9]
9. Acid-cat. Hydration [6.10]
{R: Markovnikov M } carbocation rearrangements
or (1) B2H6, Et2O (2) H2O2, NaOH, H2O [6.12]
{R: anti-Markovnikov; S: syn; }
10. Br2 or Cl2, CH2Cl2 (inert solvent) [6.15]
{R: None; S: anti; M}
11. Br2, H2O [6.18]
{R: OH to more substituted; S: anti; M}
or
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 secondary
16. 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 secondary
17. H2O (solvolysis, SN1) [Ch.8]
{S: random; M} carbocation rearrangements
tertiary, secondary
or
H2O, H2SO4, heat (SN2) [Ch.8]{S: inversion M, SN2} methyl, primary, un--branched
secondary
18.NaX, DMSO or DMF or ROH solvent (SN2) [Ch.8]
{S: inversion; M} limits on RX: Me, primary, un--branched secondary
19. 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 5.15]
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]
or
Na, 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. OsO4(cat), tBuOOH, tBuOH, HO- {S: syn} [15.4]
38. H2SO4 (Cat. SN1) with 2 ROH {M; rear} [15.7]
39. R’OH, H2SO4 (Fischer esterification) {M} [15.8]
40. (2º ROH to ketone): Na2Cr2O7, H2SO4, H2O or CrO3, H2SO4, H2O [15.10]
(1º ROH to aldehyde): CrO3, pyridine, HCl [15.10]
41. (1º ROH to acid) Na2Cr2O7, H2SO4, H2O or CrO3, H2SO4, H2O [15.10]
42. HIO4 [15.12]
43. R’O-, R’OH (Williamson ether syn) {M; S: inversion at RX} [16.6]
44. HX, Δ {M; S: yes; R: yes} [16.8]
45. HO-, H2O {M; R: yes; S: anti} [16.10]
46. HO-, H2O or H2SO4, H2O {M; S: anti} [16.12-.13]
47. RO-, ROH or ROH, H2SO4 {M; S: anti} [16.12-.13]
48. HX {M; R: yes; S: yes} [16.13]
49. (1) LiAlH4, Et2O (2) H2O {R: yes; S: yes} [16.12]
50. HO-, H2O or H2SO4, H2O
or RO-,ROH or ROH, H2SO4 {M} [17.6-.8]
51. HCN {M} [17.7]
52. R2NH {M} [17.10]
53. any oxidant, including air, CrO3, etc. [17.15]
54. RCO3H {R: yes} [17.16]
55. (1) CO2 (2) H3O+ [19.11]
56. H2O, H3O+, 
57. NaN3, DMSO or ROH
58. (1) LiAlH4, Et2O (2) H2O
59. (1) LiAlH4, Et2O (2) H2O
60. NH3 or RNH2 or R2NH, H2/Pd, or NH3 or RNH2 or R2NH, NaBH3CN