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11.1 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 Chapter 15
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11.2 Prep of Organometallic Compounds Grignard (organomagnesium compound) free radical like covalent and ionic view
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11.3 Alkyllithium OR Prep of Organometallic Compounds Grignard
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11.4 How does one make the anion of butane? Use - base(E2) or Nu: (S N 2)
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11.5 B. Rxs - protic compounds (acids - chapter 4)
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11.6 Prep of R-M (Nu: - + M) alkyl halide (sp 3 ) + metal e.g. Grignard or organomagnesium reagent But also: vinyl halide (sp 2 ) + metal aryl halide (sp 2 ) + metal
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11.7 Lithium Diorganocopper Reagents Prep and use in Synthesis (similar Grignard reagent can be made)
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11.8 Use: substitution rx, replace halides Or as anion Organometallics, alkyllithiums can be nucleophiles….. Chapter 7 and 9
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11.9 Use: substitution rx, replace halides but cuprates are better Grignards and alkyllithiums can be nucleophiles…..
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11.10 Use: Substitution, replace leaving group add eliminate* add eliminate* *not really S N 2, ignore mechanism, 2nd semester
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11.11 Primary site inverted, secondary unchanged. Rxs substitution in chapter 11
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11.12 Organometallic Compounds 15 earlier = RMgX or RLi Better
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11.13 Nucleophilic Rxs
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11.14 etc.
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11.15 Nucleophilic Rxs - important for 2nd semester carbonyl addition same product different connection
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11.16 + SM target NBS hv DMF
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11.17 SYNTHESIS SM target 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 product s
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11.18 SYNTHESIS starting material target Compare functional groups and carbon skeleton Need: 1 carbon (CN) and ketone + nitrile from olefin
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11.19 SYNTHESIS retroanalysis Br 2 H 2 Oxs SM target NC - /DMF PCC
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11.20 SYNTHESIS retroanalysis Br 2 H 2 Oxs PCC NC - /DMF RCO 3 H 1.DMSO 2.H 2 O PCC SM target
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11.21 synthesis How? “thoughts” --- join---
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11.22 synthesis plan How? synthesis reverse ?
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11.23 RCO 3 HPBr 3 Mg/THF H + /H 2 O
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11.24
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