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Organometallic Compounds (R-M)

Chapter 15. Organometallic Compounds (R-M). Organomagnesium & Organolithium compds 15.1. Lithium Diorganocopper (Gilman) Reagents 15.2. No t covered: Organopalladium reagents, Heck reaction, carbenes, carbenoids, & alkene metathesis. Synthesis, Concepts and the Final. Recall pKa of alkanes.

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Organometallic Compounds (R-M)

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  1. Chapter 15 OrganometallicCompounds(R-M) Organomagnesium & Organolithium compds 15.1 Lithium Diorganocopper (Gilman) Reagents 15.2 Not covered: Organopalladium reagents, Heck reaction, carbenes, carbenoids, & alkene metathesis. Synthesis, Concepts and the Final

  2. Recall pKa of alkanes Organometallic Compounds R-Mg-X or R-M

  3. covalent and ionic view Prep of Organometallic Compounds Grignard (organomagnesium compound) free radical like

  4. Alkyllithium OR Prep of Organometallic Compounds Grignard

  5. Reactions - protic compounds (acids)

  6. Prep of R-M (Nu:- +M) alkyl halide (sp3) + metal But also: vinyl halide (sp2) + metal aryl halide (sp2) + metal e.g. Grignard or organomagnesium reagent

  7. Nucleophilic Reactions Attacks less hindered side of epoxide

  8. Reactions Primary site inverted, secondary unchanged.

  9. (similar Grignard reagent can be made) Lithium Diorganocopper Reagents Prep and use in Synthesis

  10. Grignards and alkyllithiums can be nucleophiles….. Use: Substitution rxn, replace halides butcuprates are better

  11. add eliminate* add eliminate* Use: Substitution, replace leaving group TMS = trimethylsilyl *not really SN2, ignore mechanism, 2nd semester

  12. Better Organometallic Compounds Nucleophile attacks less hindered side of epoxide earlier = RMgX or RLi

  13. SYNTHESIS Propose how to convert starting material (sm) to a target rules: Use any number of steps For each step show: - necessary reagents - necessary conditions - expected product or products SM target

  14. SYNTHESIS Compare functional groups and carbon skeleton starting material target Need: 1 carbon (CN) and ketone + nitrile from olefin

  15. NC-/DMF PCC Br2 H2Oxs SYNTHESIS retroanalysis SM target

  16. RCO3H PCC NC-/DMF PCC DMSO H2O SYNTHESIS retroanalysis Br2 H2Oxs SM target

  17. “thoughts” --- join--- synthesis How?

  18. reverse? synthesis synthesis How? How? plan

  19. DMF NBS hv target SM +

  20. PBr3 Mg/THF RCO3H H+/H2O

  21. compare carbon skeleton functional groups convert 2-bromopropene to 2-hexanone

  22. compare carbon skeleton functional groups

  23. dibromide source? How?

  24. dibromide source? others?

  25. dibromide source? others?

  26. racemic

  27. Final 200 pts: ~130 cumulative,~70 new material 5:30 pm PSC 002, (possibly 006) chapters 1-11, 15-15.2 3 hour exam, models, pencil NO calculators or cell phones Grades submitted (VIP), scores posted ASAP. Grade - determined by either: (1) accumulated total points (tests + final + recitation pts) or (2) final exam grade WHICHEVER IS HIGHER! I’ve enjoyed teaching the class! I appreciate your hard work.

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