Chapter 15 Reactions

Question 1

Preparation of Grignard Reagents

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 1

Reactants: RX + Mg
Catalysts/Conditions: aprotic solvent (Et2O or THF)
Products: RMgX
Intermediate: none
Regioselectivity: none
Stereoselectivity: none

Question 2

Preparation of Organolithium Reagents

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 2

Reactants: RX + 2Li 
Catalysts/Conditions: solvent (Et2O or alkane like hexane)
Products: RLi + LiX
Intermediate: none
Regioselectivity: none
Stereoselectivity: none

Question 3

Preparation of Gilman Reagents with Organic Halides

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 3

Reactants: R2CuLi + R’X
Catalysts/Conditions: Et2O or THF
Products: R-R’ + RCu + LiX
Intermediate: none
Regioselectivity: rxn occurs at alkyl halide
Stereoselectivity: Inversion of Configuration at Alkyl Halide

Question 4

Reduction of Gilman Reagents with Epoxide

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 4

Reactants: 1. Epoxide + R2CuLi 2. H2O + HCl
Catalysts/Conditions: 1. Et2O
Products: Alcohol
Intermediate: None
Regioselectivity: Attack at less sub C
Stereoselectivity: Inversion of Configuration at attacked C

Question 5

Preparation of Dihalocarbene

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 5

Reactants: CHCl3 + tButOK
Catalysts/Conditions: none
Products: Cl2C: + TbutOH + Cl-
Intermediate: none
Regioselectivity: none
Stereoselectivity: none

Question 6

Addition of Carbene to an Alkene

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 6

Reactants: alkene + ChCl3 
Catalysts/Conditions: tButOK
Products: tetramethyldichlorocyclopropane
Intermediate: none
Regioselectivity: both Cls on same C
Stereoselectivity: none

Question 7

(Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity)

Answer 7

Reactants:
Catalysts/Conditions:
Products: 
Intermediate: 
Regioselectivity: 
Stereoselectivity:

Question 8

Simmons-Smith Reaction/Cyclopropanation

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 8

Reactants: R-alkene + CH2I2
Catalysts/Conditions: ZnCu
Products: R-cyclopropane
Intermediate: none
Regioselectivity: 
Stereoselectivity: stereospecific w/ respect to alkene