Alkene 1
Alkene 1
Alkene 1
Alkenes
Hydrocarbons that contain a carbon-carbon double bond.
Important roles in biology, e.g ethene- plant hormone-effect seed
germination, flower germination/fruit ripening.
Systematic nomenclature of alkenes
1.Find parent (longest chain containing a double bond) - The double bond is
numbered in the direction that gives the suffix the lowest possible no.
2. For compound with 2 double bonds, the suffix is diene
- To assign no. to substituents, count around the ring in the direction that
put the lowest no. into the name.
Special nomenclatures
The sp2 carbons of alkene called vinylic carbons
sp3 carbon that is adjacent to vinylic carbon called an allylic
carbon.
KNOCKHARDY PUBLISHING
THE STRUCTURE OF ALKENES
HOWEVER...
In ALKENES, the
three sp2 orbitals repel
each other into a
planar arrangement
and the 2p orbital lies
at right angles to them
KNOCKHARDY PUBLISHING
THE STRUCTURE OF ALKENES
KNOCKHARDY PUBLISHING
THE STRUCTURE OF ALKENES
KNOCKHARDY PUBLISHING
ORBITAL OVERLAP IN ETHENE - REVIEW
two sp2 orbitals overlap to form a sigma two 2p orbitals overlap to form a pi
bond between the two carbon atoms bond between the two carbon atoms
s orbitals in hydrogen overlap with the sp2 the resulting shape is planar
orbitals in carbon to form C-H bonds with bond angles of 120
KNOCKHARDY PUBLISHING
Since 3 points determine a plane, each sp2 C and the two atoms
singly bonded to it lie in a plane.
(a plane-defined as sp2 hybridized carbon is bonded to 3 atoms)
In order to achieve max orbital-orbital overlap, the 2 p orbitals
must be parallel.
Therefore, all 6 atoms of the double bond system are in the
same plane.
Alkenes can have cis and trans isomers
(Geometrical isomerism)
To achieve max overlap- 2 p orbitals forming the bond must be
parallel.
Therefore rotation about double bond does not readily occur. If
rotation to occur, the 2 p orbitals would cease to overlap and the
bond would break. the energy barrier to rotation about a double
bond is high.
Geometrical Isomerism
Single covalent bonds can easily rotate. What appears to be a different structure is
not. It looks like it but, due to the way structures are written out, they are the same.
ALL THESE STRUCTURES ARE THE SAME BECAUSE C-C BONDS HAVE FREE ROTATION
Animation doesnt
work in old
versions of
Powerpoint
Geometrical Isomerism
RESTRICTED ROTATION OF C=C BONDS
C=C bonds have restricted rotation so the groups on either end of the bond are
frozen in one position; it isnt easy to flip between the two.
Animation doesnt
work in old
versions of
Powerpoint
This produces two possibilities. The two structures cannot interchange easily
so the atoms in the two molecules occupy different positions in space.
Because of the high energy barrier to rotation about C-C double
bond, an alkene such as 2-butene can exist in 2 distinct form. The
H bonded to the sp2 C can be on the same side of double bond or
on opposite side of double bond.
Solubility alkenes are non-polar so are immiscible (dont mix with) with water
miscible with most organic solvents.
Exercises
Provide the proper IUPAC name for the alkene shown below.
a)
b)