This presentation discusses the reactions of organolithium compounds. Organolithium compounds undergo several reactions including: reaction with carbon dioxide to form ketones; reaction with oxygen to form hydroperoxides; reaction with esters and alkyl cyanides to form ketones; and electrophilic displacement reactions with organic halides. Electrophilic displacement, or metal-halogen exchange, is an important reaction as it allows for the synthesis of reactive organolithium compounds like vinyl lithium and phenyl lithium which can be used as precursors in organic synthesis.

1. PRESENTATION TOPIC:
ORGANOLITHIUM COMPOUNDS
PRESENTED BY:
BUSHRA ASHRAF
HETEROCYCLIC AND
ORGANOMETALLIC
COMPOUNDS

2. REACTIONS OF ORGANOLITHIUM
COMPOUNDS
 Reaction with CO2
 Reaction with O2
 Reaction with esters
 Reaction with alkyl cyanide
 Electrophilic displacement reaction

3. WITH CARBON DIOXIDE:
 When 2 molecules of organolithium compounds are treated with CO2 then
ketone is formed as a final product.
R Li + C OO R C
O
O-
Li+ R Li
R C O-
Li+
R
O-
Li+
H3O+
R C O
R

4. WITH OXYGEN:
 Alkyl lithium reacts with O2 and forms hydroperoxides.
 This reaction usually proceeds in very low yield.
 It is not good synthetic method for hydroperoxide.
H 3 O +
C H 3 C H 2 C H 2 C H 3 L i + O 2 C H 3 C H 2 C H 2 C H 2 O O -
L i +
C H 3 C H 2 C H 2 C H 2 O O H+L i O H
H y d r o p e r o x i d e

5. WITH ALKYL CYANIDE
 When organolithium compounds reacts with alkyl cyanide then imine salt
is formed which on acidic hydrolysis gives ketones.
R C N + R Li R C N
R
Li
+- H2O
R C NH
R
Imine
R C O
R
H3O+
Ketone

6. WITH ESTERS
 When esters are treated with 1 molecule of Rli then ketones are formed while
with 2 molecules of RLi, alcohols are formed as final product.
C H 3 C O C 2 H 5 + H 3 C L i H 3 C C
O -
L i +
O C 2 H 5
C H 3
H 3 O +
C H 3 C
O
C H 3
H 3 C L i
H 3 C C
O -
L i +
C H 3
H 3 O +
H 3 C C
O H
C H 3
C H 3C H 3
O

7. ELECTROPHILIC DISPLACEMENT
 Organolithium compounds undergoes electrophilic displacement by the
reaction with organic halides.
 It is also known as metal-halogen exchange reaction.
 The general reaction is given as:
R X + R'
Li R Li R'
X+

8. IMPORTANCE OF ELECTROPHILIC DISPLACEMENT:
 Electrophilic displacement reaction is useful for the synthesis of 2 important
compounds that are used as precursor for the synthesis of different organic
compounds which are as follows:
 Vinyl lithium:
Br Li+ Li Br+
vinyllithiumVinylbromiden-butyllithium n-butylbromide
 Phenyl lithium:
Cl
+ Li Cl
Li
+
phenyl lithiumn-butyl lithium n-butyl chloride