cr6mapans - /ROH or KOH/EtOH{R: Zaitsev; S: anti; M } 5. H...

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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 PBr 3 or SOCl 2 [4.13] 2. X 2 , hv {M} [4.14] 3. Acid-cat. Dehydration [5.9] {R: Zaitsev; M} carbocation rearrangements 4. E2 elimination [5.15] typically RO -
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Unformatted text preview: /ROH or KOH/EtOH{R: Zaitsev; S: anti; M } 5. H 2 , 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 [6.8] {R: anti-Markovnikov; S: random; M } 7. H 2 SO 4 , {M; R: Mark; S: random} [6.9] 8. H 2 O, [6.9] 9. Acid-cat. Hydration [6.10] {R: Markovnikov M } carbocation rearrangements or (1) B 2 H 6 , Et 2 O (2) H 2 O 2 , NaOH, H 2 O [6.12] {R: anti-Markovnikov; S: syn; } 10. Br 2 or Cl 2 , CH 2 Cl 2 (inert solvent) [6.15] {R: None; S: anti; M} 11. Br 2 , H 2 O [6.18] {R: OH to more substituted; S: anti; M} 12. RCO 3 H [6.19] {S: syn, with retention at alkene E/Z } 13. (1) O 3 , CH 2 Cl 2 , -78C (2) Me 2 S or Zn [6.20] 14. (1) O 3 , CH 2 Cl 2 , -78C (2) H 2 O [6.20]...
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This note was uploaded on 05/05/2011 for the course BIOL 400 taught by Professor Dr.biology during the Spring '11 term at University of Tennessee.

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