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OrganometallicOrganometallic
CompoundsCompounds
Dr. Bapu R Thorat
Victor GrignardVictor Grignard
Grignard ReagentsGrignard Reagents
Grignard, Victor , 1871–1935, French chemist. He shared the
1912 Nobel Prize in Chemistry1912 Nobel Prize in Chemistry for his work in organic synthesis
based on his discovery (1900) of the Grignard Reagent. He taught
at the Univ. of Nancy (1909–19) and at the Univ. of Lyons (from
1919 until the end of his career).
R X + Mg R MgX
dry ether
Mg
Br
MgBr
H
I
H
MgI
Cl
MgCl
N
Cl
N
MgCl
The alkyl halides are more reactive than aryl and vinyl halides.
The reactivity of alkyl halide is RI > RBr > RCl whereas
organomagnesium fluoride are not known yet.
Solvents:
diethyl ether (b.p. 34.60
C),
diethylene glycol,
diglyme (b.p. 1600
C),
tetrahydrofuran (b.p. 660
C)
Grignard ReagentsGrignard Reagents
Halide does not contain the following functional groups –
Functional group with active hydrogen –COOH, -C≡CH, -OH, -NH2, -SH, etc
The functional group - -CO-, -CN, -NO2, -SO-, Epoxide, etc.
Grignard Reagents - StructureGrignard Reagents - Structure
The Grignard reagent was existing in dimeric form (stabilization of Grignard
reagent) which is in equilibrium with dialkyl magnesium compound and
magnesium dihalide.
R MgX2 R2Mg + MgX2 R Mg
X
Mg R
X
The X-ray diffraction studies - R Mg
X
Mg R
X
OEt2
OEt2
OEt2
OEt2
Organometallic NomenclatureOrganometallic Nomenclature
C C
H
H MgBr
H
vinylmagnesium bromide
H3CH2CH2CH2C-Li
Butyllithium
(H3C)2Cu- Li+
Dimethylcopper lithium
H3C MgBr
methylmagnesium bromide
CH MgBr
H3C
H3C
H2C Mg
Br
MgBr
phenylmagnesium bromide
isopropylmagnesium bromide
benzylmagnesium bromide
C Mg
BrH2C
CH3
CH3
H
(R)-sec-butylmagnesium bromide
Organometallic compounds were normally named as substituted metals. e.g. alkyl
metal or alkyl metal halide.
• The difference in electronegativity between carbon and magnesium (lithium), the C-MgThe difference in electronegativity between carbon and magnesium (lithium), the C-Mg
(C-Li) bond is polar covalent, with C(C-Li) bond is polar covalent, with Cδδ--
and Mgand Mgδδ++
((LiLiδδ++
))
– Grignard and organolithium reagents behave like carbanions/nucleophile
• CarbanionCarbanion: an anion in which carbon has an unshared pair of electrons and bears a: an anion in which carbon has an unshared pair of electrons and bears a
negative charge.negative charge.
Grignard and Organolithium Reagents – ReactivityGrignard and Organolithium Reagents – Reactivity
• The carbon-lithium bond in CH3Li has about 40% ionic character, and the carbon-
magnesium bond in CH3MgCl has about 35% ionic character. Therefore organolothium
are more reactive than Girgnard reagent.
phenylmagnesium bromide
MgBr
Br
Mg/dry ether
H + MgBr(OH)
H2O
ROH
H + MgBr(OR)
O2
OOMgBr OOH
HCl
OH
D2
O
D + MgBr(OD)
RCOOH
H + MgBr(OOCR)
Reactivity of Grignard reagent
with active hydrogen
Grignard Reagents – ReactivityGrignard Reagents – Reactivity
phenylLithium
Li
H
Li/dry ether
H + LiOH
H2O
ROH
H + LiOR
O2
OOLi OOH
HCl
OH
D2
O
D + LiOD
RCOOH
H + RCOOLi
Reactivity of organolithium
reagent with active hydrogen
RNH2
H + RNHLi
Organolithium Reagents – ReactivityOrganolithium Reagents – Reactivity
formaldehydeformaldehyde to give primary alcoholsto give primary alcohols
aldehydesaldehydes to give secondary alcoholsto give secondary alcohols
ketonesketones to give tertiary alcoholsto give tertiary alcohols
estersesters to give tertiary alcoholsto give tertiary alcohols
COCO22 to give acidsto give acids
epoxides to give primary alcoholsto give primary alcohols
cyanidecyanide to ketone or acidto ketone or acid
Grignard reagents react productively with:Grignard reagents react productively with:
phenylmagnesium
bromide
MgBr
Reaction of
Grignard reagent
H
O
H
Formaldehyde
Aldehyde
Ketone
Carboxylic
acid
Ester
Cyanide
CO2
Epoxide
R
O
H
R
O
R1
R
O
OH
R
O
OR1
RN
O
R
H
O
H
MgBr
H3O+
H
OH
H
10
Alcohol
R
O
H
MgBr
H3O+
R
OH
H
20
Alcohol
R
O
R1
MgBr
H3O+
R
OH
R1
30
Alcohol
R
O
OMgBr Very slowly
react with GR
R
O
OR1
MgBr
H3O+
R
O
+ MgBr(OR1)
GR
R
O
MgBr
R O HR
N
MgBr H 3
O
+
O
O
MgBr
H3O+
O
HO
BrMgO
R
H3O+
HO
R
10
Alcohol
30
Alcohol
Carboxylic
acid
Grignard reagents - ReactionsGrignard reagents - Reactions
phenyllithium
Li
Reaction of
Organolothium reagent
H
O
H
Formaldehyde
Aldehyde
Ketone
Carboxylic
acid
Ester
Cyanide
CO2
Epoxide
R
O
H
R
O
R1
R
O
OH
R
O
OR1
RN
O
R
H
O
H
Li
H3O+
H
OH
H
10
Alcohol
R
O
H
Li
H3O+
R
OH
H
20
Alcohol
R
O
R1
Li
H3O+
R
OH
R1
30
Alcohol
R
O
OLi
R
O
OR1
Li
H3O+
R
O
+ LiOR1
R
O
Li
R O HR
N
Li H 3
O
+
O
O
Li
H3O+
O
HO
LiO
R
H3O+
HO
R
10
Alcohol 30
Alcohol
Carboxylic
acid
PhLi
PhLi
R
O
OLi
Li
R
O
Ketone
Organolithium reagentsOrganolithium reagents
- Reactions- Reactions
phenylmagnesium
bromide
MgBr
Br
Mg/dry ether
CH(OEt)3
CH(OEt)2
H3O+
CHO
ortho-ether
amide
HOCNMe2
H
OMgBr
NMe2
H3O+
CHO
H H
H MgBr +
H
SO2
S
O
OMgBr
H3O+
SO2H
SiCl4 Ph2SiCl2
H2O
Si O Si
Ph
PhPh
Ph
PCl3 Ph3P
AgBr
CoCl2
Ph2Cd
or CoCl2
R1Cl
R1
O
Ph
Cl
O
Ph
cold
O
OMgBr
OMgBr
+
Reactions of
Grignard reagent
Grignard reagents - ReactionsGrignard reagents - Reactions
End of Lecture. Any Questions?

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