CARBENE

Organic Chemistry

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POINTS TO STUDY:
1. Definition
2. Structure and bonding
3. Reactivity
4. Generation of Carbenes
5. Application
 Definition:
A Carbene is a highly reactive species containing
a carbon atom with six valence electrons
having the general formula:
RR’C:
practically all having lifetimes considerably
under 1 sec.
A Carbene is a molecule containing a neutral
carbon atom with a valence of two and two
unshared valence electrons
Structure and Bonding:
Singlet and Triplet carbenes:
A carbene is a divalent carbon atom with
two electrons that are not shared with any
other atoms.
Triplet carbenes are generally stable in the
gaseous state, While singlet Carbenes occur
more often in aqueous media.
The terms singlet and triplet come from the
field of Spectroscopy.
Difference between Singlet and Triplet
Carbenes :
Singlet Carbene Triplet Carbene
 When the two electrons have  When they have parallel
opposite spins which is called spins, The carbene is called
singlet carbene. Triplet Carbene.
 A singlet carbene has a pair of  A triplet carbene has two
electrons in a single orbital in unpaired electrons in distinct
its ground state. orbital.
 +1/2-1/2=0  +1/2+1/2=1
 Then 2s+1=2(0)+1= 1(singlet)  Then 2s+1=2(1)+1= 3 (Triplet)
3. Reactivity
 Carbenes are highly reactive hexavalent species
that exist in two spin states, i.e. in a singlet form in
which two electrons are paired up and in a triplet
form in which two electrons remain unpaired. Of
the two, the singlet form is more reactive one.
 Singlet carbene is generally participate in cheletropic
reactions. Singlet carbenes with unfilled p-orbital
should be electrophilic.
 Triplet carbenes can be considered to be diradicals,
and participate in stepwise radical additions.
Addition to C C:
Insertion reaction:
Generation of Carbenes:
The synthesis of carbene molecules is
generally based on elimination and
fragmentation reactions.
Carbenes are formed as intermediate
products when groups attached to the
carbon atom are broken as a result of
photolysis, thermolysis or reaction with
metals.
1. Carbenes from diazo compounds:
R hv R
R RN2 : N2
2.Carbenes formation by α-
elimination:
NaOH
CHcl3 Ccl3 l
-H+
Application of Carbenes:
Industrial production of Tetrafloaroethylene.
Thanks for visit…
Presented by:
Taskinfatma M. Saiyed.
F.Y.M.Sc(Analytical batch)
22-pch-075
Semester -1