Ethers, Sulfides and Epoxides - 11

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Chapter 15
Organometallic Compounds (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
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Prep of Organometallic Compounds
Grignard (organomagnesium compound)
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Prep of Organometallic Compounds
Grignard
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How does one make the anion of butane?
Use - base(E2) or Nu (SN2)
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B. Rxs - protic compounds (acids - chapter 4)
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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
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Lithium Diorganocopper Reagents Prep and use in
Synthesis
(similar Grignard reagent can be made)
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Use substitution rx, replace halides
Organometallics, alkyllithiums can be
nucleophiles.. Chapter 7 and 9
Or as anion
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Use substitution rx, replace halides
Grignards and alkyllithiums can be nucleophiles..
but cuprates are better
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Use Substitution, replace leaving group
not really SN2, ignore mechanism, 2nd semester
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Rxs substitution in chapter 11
Primary site inverted, secondary unchanged.
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Organometallic Compounds 15
earlier RMgX or RLi
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Nucleophilic Rxs
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Nucleophilic Rxs - important for 2nd semester
carbonyl addition
same product different connection
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target
SM

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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
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SYNTHESIS
Compare functional groups and carbon skeleton
starting material
target
Need 1 carbon (CN) and ketone nitrile from
olefin
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SYNTHESIS
retroanalysis
SM
target
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SYNTHESIS
retroanalysis
Br2 H2Oxs
SM
target
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synthesis
How?
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synthesis
synthesis
How?
How?
plan
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H/H2O
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