Exam 1 - Organometallics

Question 1

___ - Neutral carbons with a lone pair (no octet though!)

Answer 1

Carbenes

Question 2

Organometallics add to the ___ substituted side of the epoxide.

Answer 2

less

Question 3

Gilman Reagents (Organocuprates) use ___ instead of MgX.

Answer 3

CuX

Question 4

In the Simmons-Smith Reaction, you add ___ and ___ to an alkene to create a regular cyclopropane and ___ byproduct.

Answer 4

CH2I2 and Zn(Cu), ZnI2

Question 5

Carbenes - Neutral carbons with a ___ ___ (no ___ though!)

Answer 5

lone pair, no octet

Question 6

___ -> Compound that delivers elements of a carbene without producing a free carbene.

Answer 6

carbanoid

Question 7

Cycloproponation is ___. AKA the alkene geometry will determine which side the groups will end up on.

Answer 7

stereospecific

Question 8

Grignard Reagents CANNOT work with any ___ ___ around!!! (i.e. OH).

Answer 8

acidic Hs

Question 9

No protecting groups are needed for -OH groups if using ___ ___.

Answer 9

Gilman Reagents

Question 10

In Organo-Lithium Reagents, the Cs behave as ___.

Answer 10

carboanions

Question 11

Organometallics revolve around ___-___ type bonds.

Answer 11

C-M (where M is metal)

Question 12

Grignard Reagents do not work well if one or more epoxide Cs are ___.

Answer 12

quaternary

Question 13

Grignard Reagent reactions require a ___ ___ for ___, as no acidic protons can be around for the first reaction.

Answer 13

separate work-up, H3O+

Question 14

Grignard Metal Reagents are very ___.

Answer 14

basic

Question 15

Grignard Reagents attack the ___ substituted side of the epoxide.

Answer 15

less

Question 16

Gilman Reagents have ___ of stereochemistry via a ___ mechanism.

Answer 16

inversion, SN2

Question 17

If you treat an alkene with ___ and ___, you can create a cyclopropane with 2 Cl groups attached.

Answer 17

KOtBu, CHCl3

Question 18

The ___ reaction creates a regular cyclopropane.

Answer 18

Simmons-Smith Reaction

Question 19

___ ___ are very basic.

Answer 19

Grignard Reagents

Question 20

Carboanion stability ordered from most to least:

Answer 20

alkyne (sp) > alkene (sp2) > alkane (sp3)

Question 21

Gilman Reagents attack the ___ substituted side of the epoxide.

Answer 21

less

Question 22

You can use ___ equivalents of Gilman Reagent if an -OH is present. However, it is usually just better to add a ___ ___.

Answer 22

2 equivalents, protecting group

Question 23

Grignard Reagents lead to ___ of the stereochemistry via ___.

Answer 23

inversion, SN2

Question 24

Most organometallics are ___, so they CANNOT react with ___ or acidic Hs.

Answer 24

basic, H2O

Question 25

Grignard Reagents include Mg___,___,___

Answer 25

Br,I,Cl

Question 26

Gilman Reagents are ___ ___ than Grignard Reagents, thus they can work around ___ ___.

Answer 26

less basic, acidic Hs

Question 27

Carbenes are ___ - both electrophilic and nucleophilic at the same time.

Answer 27

amphilic

Question 28

In C-X, the carbon acts as a ___. In C-M, the carbon acts as a ___.

Answer 28

electrophile, nucleophile

Question 29

(o) means ___.

Answer 29

metal

Question 30

Gilman Reagent reactions are ___.

Answer 30

stereospecific

Question 31

Order of reactivity from most to least for Lithium Halogen Exchange:

Answer 31

I > Br > Cl > F