Ch. 23: Organometallic Compounds

Question 1

Preparation of Organolithium Compound

Answer 1

Li (2 eq.) (starting with R-X, ending with R-Li)

Question 2

Preparation of Organomagnesium Compound

Answer 2

Mg, Et2O (starting with R-X, ending with R-Mg-X)

Question 3

Preparation of Gilman Reagent

Answer 3

1. Li (2 eq) 2. CuX (0.5 eq)
   (Gilman Reagent: R2CuLi)

Question 4

Gilman Coupling yields…

Answer 4

R’-R (+ RCu + LiX)

Question 5

Simmons-Smith Reaction (triangle)

Answer 5

CH2I2, Zn-Cu, Et2O (stereospecific)

Question 6

Still: Preparation of Organostannanes

Answer 6

1. Mg, Et2O 2. Bu3SnCl (R-X to
   R-SnBu3)

Question 7

Stille: Organostanne coupling yields…

Answer 7

R-R’ (+ X-SnBu3)
Reagent: Pd(PPh3)4 or Pd(OAc)2

Question 8

Suzuki: preparation of organoboron compounds

Answer 8

R: Catecholborane or 9-BBN
Li: B(OMe)3

Question 9

Suzuki: Organoboron coupling yields…

Answer 9

R-R’ (+ X-BY2)
Reagent: Pd(PPh3)4, NaOEt

Question 10

Negishi: Preparation of Organozinc compounds

Answer 10

ZnBr2 or Zn, Et2O (replaces X with ZnBr)

Question 11

Negishi: Organozinc coupling yields….

Answer 11

R-R’ (+ ZnX2)
Reagent: Pd(PPh3)4

Question 12

Heck reaction reagent

Answer 12

Pd(PPh3)4 or Pd(OAc)2, Base

Question 13

Heck reaction yields

Answer 13

R-Alkene (+ HX)

Question 14

Alkene Metathesis

Answer 14

Reagent: catalyst
Always yields byproduct CH2=CH2

Question 15

Ring-Closing Metathesis

Answer 15

Reagent: Grubbs catalyst
Always yields byproduct CH2=CH2

Question 16

Ring Opening Metathesis

Answer 16

Reagent: Grubbs catalyst, CH2=CH2)