This document provides an introduction to organometallic compounds and reagents. It discusses that organometallic compounds contain carbon-metal bonds and some important examples. Organometallic reagents of magnesium, lithium, and copper are important for stoichiometric and industrial reactions. The document also summarizes key reactions of organolithium, Grignard, and organocopper reagents that involve nucleophilic addition or substitution. Finally, it recognizes three great contributors to the field of organometallic chemistry.

1. ORGANOMETALLIC
COMPOUNDS AND
REAGENTS
MD. HASIB KHAN
ID:2017-1-70-022
DEPARTMENT OF PHARMACY
EAST WEST UNIVERSITY

2. INTRODUCTION OF ORGANOMETALLIC
COMPOUNDS
• ORGANOMETALLIC COMPOUNDS ARE THE COMPOUNDS WHICH CONTAIN ORGANIC
COMPOUND ASSOCIATED WITH METAL. IT CONTAINS CARBON- METAL BOND (R-M).
• ORGANOMETALLIC COMPOUNDS OF Mg, Li, AND Cu ARE THE MOST IMPORTANT
ORGANOMETALLIC REAGENTS.
• ORGANOMETALLIC COMPOUNDS ARE WIDELY USED BOTH STOICHIOMETRICALLY IN
RESEARCH AND INDUSTRIAL CHEMICAL REACTIONS.
• FERROCENE, COBALTOCENE, TRIMETHLYALUMINIUM, DIMETHYLZINC ARE SOME
IMPORTANT ORGANOMETALLIC COMPOUND.

3. ORGANOMETALLIC REAGENTS
THE KEY CONCEPTS:
MAKE A CARBON NEGATIVELY
CHARGED/POLARIZED SO IT IS NUCLEOPHILIC.
REACTION WITH ELECTROPHILIC CARBON CAN
MAKE CARBON-CARBON BONDS.
THIS IS A BIG DEAL!

4. NOMENCLUTURE OF ORGANOMETALLIC
COMPOUNDS
Organometallic compounds are normally named as substituted metal,
e.g. alkyl metal or alkyl metal halide. So, the metal is the parent.
•CH3CH2MgCH2CH3 Diethyl magnesium
•H2C=CHNa (Vinyl sodium)
•CH3MgI (Methyl magnesium iodide)
•Li (Cyclopropyl lithium)
•ch3Mgbr ( methyl magnesium bromide)

5. ORGANOLITHIUM REAGENTS
• ORGANOLITHIUM REAGENTS ARE ORGANOMETALLC COMPOUNDS THAT CONTAIN
CARBON-LITHIUM BONDS.
• THEY ARE USED TO TRANSFER THE ORGANIC GROUP IN SYNTHETIC STEPS (ORGANIC
SYSTHESIS).
• ORGANOLITHIUM REAGENTS ARE USED AS AN INITIATOR FOR ANIONIC
POLYMERIZATION AND APPLIED IN ASYMMETRIC SYNTHESIS IN THE
PHARMACEUTICAL INDUSTRY.
PREPARATION OF ORGANOLITHIUM REAGENTS
RX + 2LI RLI + LIX
• WE USE PENTANE OR HEXANE AS SOLVENTS FOR THIS REACTION.
• REACTIVITY :I > BR > CL >> F, RX > ARX.

6. GIRGNARD REAGENTS
• THE GRIGNARD REACTION IS AN ORGANOMETALLIC CHEMICAL REACTION IN WHICH
ALKYL, VINYL, OR ARYL-MAGNESIUM HALIDES (GRIGNARD REAGENTS) ADD TO A
CARBONYL GROUP IN AN ALDEHYDE OR KETONE.
• THIS REACTION IS AN IMPORTANT TOOL FOR THE FORMATION OF CARBON–CARBON
BONDS. THE REACTION OF AN ORGANIC HALIDE WITH MAGNESIUM IS NOT A GRIGNARD
REACTION, BUT PROVIDES A GRIGNARD REAGENT.
RX + MG RMGX
• ANHYDROUS DIETHYL ETHER OR THF ARE USED AS SOLVENTS FOR THIS
REACTION.
• REACTIVITY :I > BR > CL >> F, RX > ARX. (SAME AS ORGANOLITHIUM
REAGENTS)

7. ORGANOCOPPER REAGENTS
• LITHIUM DIORGANOCOPPER REAGENTS, KNOWN MORE COMMONLY AS
GILMAN REAGENTS
• PREPARED BY TREATING AN ALKYL, ARYL, OR ALKENYL LITHIUM COMPOUND
WITH CU(I) IODIDE.
2RLI + CUX R2CULI + LIX

8. IMPORTANT REACTION OF ORGANOMETALLIC
REAGENTS
NORMALLY ORGANOMETALLIC COMPOUNDS SHOW NUCLEOPHILIC REACTION.
SUCH AS, NUCLEOPHILIC SUBSTITUTION, NUCLEOPHILIC ADDITION,
NUCLEOPHILIC ACYL SUBSTITUTION.
REACTION OF RLI OR RMGX WITH ALDEHYDES AND KETONES. REACTIONS OF RLI OR RMGX
WITH ESTERS

9. REACTIONS OF GIRGNARD REAGENTS

10. THREE GREAT CONTRIBUTOR OF ORGANOMETALLIC
CHEMISTRY