Exam 1 - Organometallics Flashcards
___ - Neutral carbons with a lone pair (no octet though!)
Carbenes
Organometallics add to the ___ substituted side of the epoxide.
less
Gilman Reagents (Organocuprates) use ___ instead of MgX.
CuX
In the Simmons-Smith Reaction, you add ___ and ___ to an alkene to create a regular cyclopropane and ___ byproduct.
CH2I2 and Zn(Cu), ZnI2
Carbenes - Neutral carbons with a ___ ___ (no ___ though!)
lone pair, no octet
___ -> Compound that delivers elements of a carbene without producing a free carbene.
carbanoid
Cycloproponation is ___. AKA the alkene geometry will determine which side the groups will end up on.
stereospecific
Grignard Reagents CANNOT work with any ___ ___ around!!! (i.e. OH).
acidic Hs
No protecting groups are needed for -OH groups if using ___ ___.
Gilman Reagents
In Organo-Lithium Reagents, the Cs behave as ___.
carboanions
Organometallics revolve around ___-___ type bonds.
C-M (where M is metal)
Grignard Reagents do not work well if one or more epoxide Cs are ___.
quaternary
Grignard Reagent reactions require a ___ ___ for ___, as no acidic protons can be around for the first reaction.
separate work-up, H3O+
Grignard Metal Reagents are very ___.
basic
Grignard Reagents attack the ___ substituted side of the epoxide.
less
Gilman Reagents have ___ of stereochemistry via a ___ mechanism.
inversion, SN2
If you treat an alkene with ___ and ___, you can create a cyclopropane with 2 Cl groups attached.
KOtBu, CHCl3
The ___ reaction creates a regular cyclopropane.
Simmons-Smith Reaction
___ ___ are very basic.
Grignard Reagents
Carboanion stability ordered from most to least:
alkyne (sp) > alkene (sp2) > alkane (sp3)
Gilman Reagents attack the ___ substituted side of the epoxide.
less
You can use ___ equivalents of Gilman Reagent if an -OH is present. However, it is usually just better to add a ___ ___.
2 equivalents, protecting group
Grignard Reagents lead to ___ of the stereochemistry via ___.
inversion, SN2
Most organometallics are ___, so they CANNOT react with ___ or acidic Hs.
basic, H2O
Grignard Reagents include Mg___,___,___
Br,I,Cl
Gilman Reagents are ___ ___ than Grignard Reagents, thus they can work around ___ ___.
less basic, acidic Hs
Carbenes are ___ - both electrophilic and nucleophilic at the same time.
amphilic
In C-X, the carbon acts as a ___. In C-M, the carbon acts as a ___.
electrophile, nucleophile
(o) means ___.
metal
Gilman Reagent reactions are ___.
stereospecific
Order of reactivity from most to least for Lithium Halogen Exchange:
I > Br > Cl > F
