Hydroarbons - Notes

GRADE 11 – HYDROCARBONS
Conformations: In alkanes C-C bonds permit free rotation about C-C single bond. This rotation results in
different spatial arrangement of atoms in space.
The spatial arrangements of atoms which can be converted into one another by rotation around a C-C
single bond is called conformations.
Rotation around C-C single bond is not completely free. It is hindered by a small energy barrier due
to weak repulsive interaction between adjacent bonds. The repulsive interaction is called torsional strain.
CONFORMATIONS OF ETHANE:
Eclipsed conformation: conformation in which hydrogen atoms are attached to two carbon atoms are as
close together as possible.
Staggered conformation: conformation in which hydrogen atoms attached to two carbon atoms are as far
apart as possible.
Skew conformation: the indefinite intermediate conformations between eclipsed and staggered
conformations are called skew conformations.
Representations of eclipsed and staggered conformations:
a) Saw Horse Projections:
b) Newman projections:
Relative stability of conformations:

In staggered form of ethane, the electron clouds of carbon-hydrogen bonds are as far apart as possible. Thus,
there are minimum repulsive forces, minimum energy and maximum stability of the molecule. On the other
hand, when the staggered form changes into the eclipsed form, the electron clouds of the carbon – hydrogen
bonds come closer to each other resulting in increase in electron cloud repulsions. Hence, molecule will have
to possess more energy and thus has lesser stability.
As already mentioned, the repulsive interaction between the electron clouds, which affects stability of a
conformation, is called torsional strain. Magnitude of torsional strain depends upon the angle of rotation
about C–C bond. This angle is also called dihedral angle or torsional angle. Of all the conformations of
ethane, the staggered form has the least torsional strain and the eclipsed form, the maximum torsional strain.
Geometrical isomerism:
The rotation around C=C bond is not free. It is restricted. As a result, groups around the doubly bonded
carbon atoms gives rise to different geometries of such compounds. The stereoisomers of this type are called
geometrical isomers.
The isomer in which two identical atoms or groups lie on the same side of the double bond is called cis
isomer. The other isomer in which identical atoms or groups lie on the opposite sides of the double bond is
called trans isomer. Thus, cis and trans isomers have the same structure but have different configuration
(arrangement of atoms or groups in space).
Geometrical or cis-trans isomers of but-2-ene

Cis form of alkene is found to be more polar than the trans form. In the trans-but-2-ene, the two methyl
groups are in opposite directions, Therefore, dipole moments of C-CH3 bonds cancel, thus making the trans
form non-polar.
In the case of solids, it is observed that the trans isomer has higher melting point than the cis form. This is
due to the symmetrical packing of trans isomer.
Q 1: Draw cis and trans isomers of the following compounds. Also write their IUPAC names :
i)CHCl = CHCl
ii) C2H5CCH3 = CCH3C2H5
Q 2: Which of the following compounds will show cis-trans isomerism?

i) (CH3)2C = CH – C2H5
ii) CH2 = CBr2
iii) C6H5CH = CH – CH3
iv) CH3CH = CCl CH3
Structure of Benzene:
The molecular formula of benzene, C6H6, indicates a high degree of unsaturation.
Resonance and stability of benzene: The concept of oscillating double bonds in benzene is explained by
resonance. Benzene is a hybrid of various resonating structures. The two structures, given by Kekulé are the
main contributing structures. The hybrid structure is represented by inserting a circle or a dotted circle in the
hexagon. The circle represents the six electrons which are delocalized between the six carbon atoms of the
benzene ring.
All the six carbon atoms in benzene are sp2 hybridized. Two sp2 hybrid orbitals of each carbon atom overlap
with sp2 hybrid orbitals of adjacent carbon atoms to form six C—C sigma bonds which are in the hexagonal
plane. The remaining sp2 hybrid orbital of each carbon atom overlaps with s orbital of a hydrogen atom to
form six C—H sigma bonds. Each carbon atom is now left with one unhybridised p orbital perpendicular to
the plane of the ring. The unhybridised p orbital of carbon atoms are close enough to form a π bond by
lateral overlap.
The six π electrons are thus delocalised and can move freely about the six carbon nuclei, instead of any two.
The delocalised π electron cloud is attracted more strongly by the nuclei of the carbon atoms than the
electron cloud localised between two carbon atoms. Therefore, presence of delocalised π electrons in
benzene makes it more stable. X-ray data indicates that all the six C—C bond lengths are of the same order
(139 pm) which is intermediate between C— C single bond (154 pm) and C—C double bond (133 pm).
Thus, the absence of pure double bond in benzene accounts for the reluctance of benzene to show addition
reactions under normal conditions, thus explaining the unusual behaviour of benzene.

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GRADE 11 – HYDROCARBONS

Representations of eclipsed and staggered conformations:

a) Saw Horse Projections:

Relative stability of conformations:

Geometrical or cis-trans isomers of but-2-ene

Q 2: Which of the following compounds will show cis-trans isomerism?

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