Advices For Studying Organic Chemistry

ORGANOLITHIUM AND GRIGNARD REAGENTS

(SECTION 12.3)

R

12.11C FORMATION OF

—X + 2 Li R—Li + LiX

R—X + Mg R—MgX

AND ORGANOLITHIUM REAGENTS

(SECTION 12.7 AND 12.8)

12.11D REACTIONS OF GRIGNARD

HA R H +M+A−

(attack at least hindered carbon) R CCOH

HCH

O

HC

OH

H

R

R' C H

O

R' C

C

OH

H

R' R"

O

R C

OH

R"

R

R' C OR"

O

R'

OH

R

R

C

'

R

+ HOR"

R M

O

1. 
   
   
   
   2. H 3 O+
   
   
   
   

(M = Li or MgBr)

1. 
   
   
   
   2. H 3 O+
   
   
   
   


2. 
   
   
   
   2. H 3 O+
   
   
   
   


3. 
   
   
   
   2. NH 4 Cl, H 2 O
   
   
   
   


4. 
   
   
   
   2. NH 4 Cl, H 2 O
   
   
   
   

12.11E COREY-POSNER, WHITESIDE-HOUSE SYNTHESIS (SECTION 12.9)

2 RLi + CuI R 2 CuLi (^) (R' = 1Ro or' 2 Xo, cyclic) R—R’ + RCu + LiX