Drawbacks of Open Chain Structure

The molecular formula of benzene has been found from analytical data, to be C6H6.
Relatively higher proportion of

carbon and addition of chlorine to benzene molecule indicate it to be an unsaturated compound. Depending on the
various facts available to scientists from time to time, many structures for benzene had been proposed. Some are
described below.
Open Chain Structure

Based upon observable facts given above and the tetravalency of carbon, the following open chain structures were
proposed for benzene.
Drawbacks of open chain structure

The open chain structure for benzene was rejected due to the following reasons:
• Addition reactions usually given by alkenes and alkynes are not given by benzene.
• Benzene forms only one kind of monosubstituted product. An open chain structure however, can form more
than one kind of monosubstituted product as shown below:
• The open chain compounds do, not give reactions such as Friedel-Craft reaction, nitration, sulphonation.
• On reduction with hydrogen in the presence of Ni at 200°C, actually a cyclic compound cyclohexane is
obtained.
These facts suggest a ring structure for benzene.
Ring structure of benzene

After taking into account account the above observed facts, Kekule (1865) suggested a ring structure for benzene.
According to him, six carbon atoms occupied six corners of a regular hexagon in benzene and each carbon carried
one hydrogen atom. To satisfy the tetravalency of carbon, the system consisted of alternate single and double bonds.
Kekule's formula is shown below.
Defects in Kekule's formula
While Kekule's formula explained most of theory served facts for benzene, it could still not explain the following facts,
• The saturated nature of benzene.
• In actuality only one kind of ortho derivatives are known, but according to Kekule's formula, there can be two
ortho positions.
The defect of having two ortho positions was explained by proposing that the positions of the double bonds in
benzene are not fixed. Instead, the double bonds in the benzene molecule keep changing their positions and thus all
positions in benzene molecule become identical.
Chemists generally used the Kekule's structure as late as 1945. Many ring structures for benzene have been
proposed after Kekule's structure. Some of them are,
Claus diagonal Dewar'sformula(1867) formula(1867)
Resonance hybrid structure of benzene

The currently accepted structure was developed by the application of the theory of resonance proposed in 1933. This
theory states that benzene is a resonance hybrid of the following canonical forms.
Since, the forms I and II are the most contributing, hence benzene is represented as a hybrid structure of these two
structures, i.e.,
Resonance hybrid
Evidences which support resonance structure of benzene

The following facts support the resonance structure of benzene:
• The carbon-carbon bond length in benzene is identical at 139 pm, for all bonds. This value is intermediate
between the bond lengths for C-C bond (154 pm) and C = C (134 pm).
• A regular hexagonal structure for benzene is obtained by X-ray diffraction, which gives a C-C bond length of
139 pm.
Large resonance energy

Due to resonance, the p-electron charge in benzene gets distributed over greater area, i.e., gets delocalized.
Delocalization results in the energy of the resonance hybrid decreasing relative to the contributing structures, by
about 150 kJ mol-1. This decrease in energy is called resonance energy. The unusual stability of benzene is due to
this resonance stabilization.
Orbital structure of benzene

X-ray studies show that a
• Benzene molecule is a flat (planar) molecule. All carbon and hydrogen atoms lie in the same plane.
• It has a regular hexagon structure with all six carbon atoms lying at the corners; each carbon atom is bonded
to three other atoms.
• All carbon-carbon bond lengths are equal at 139 pm.
• All CC angles (or CH angles) are equal at 120°.

These results indicate that each carbon atom in benzene molecule is sp 2 hybridized. All sp2 hybrid orbitals lie in the
same plane (the plane of the carbon atoms) and are oriented towards the corners of an equilateral triangle. Thus,
each carbon in benzene has three sp2 hybrid orbitals lying in the same plane and one -unhybridized 'p' orbital.
(a) Formation of a planar hexagonal structure due to overlapping of the sp2 hybrid orbital of each carbon atom with its
neighboring carbon atoms and hydrogen atoms.
(b) A unhybridized 2p orbital on each carbon lies perpendicular to the carbon-carbon plane.
Out of the three hybrid orbitals, two overlap axially with the orbitals of the neighboring carbon atoms on either sides to
form C-C 's' bonds. The third, sp2 hybridized orbital of the carbon atom overlaps with the half-filled '1s' orbital of the
hydrogen atom forming a 's' C-H bond.
A planar hexagonal structure is formed when six carbons are placed in a hexagonal geometry, the orbital overlapping
leads to the structure (a).
In (b), each carbon is left with one unused '2p' orbital at right angle, to the hexagon. These unused '2p' orbitals of
carbon atoms overlap each other sideways, and form carbon-carbon p-bonds. As the system is completely
symmetrical, the '2p' orbitals can overlap sideways equally well with either of the neighboring carbon atoms. Hence
sideways overlapping of '2p' orbitals of carbon atoms can form two sets of
p-bonds as shown.
Sideways overlap of 2p orbitals leading to formation of two sets of p-bonds.
All the 'p' orbitals on the six C atoms in benzene molecule are equidistant from each other. Thus 'p' orbitals of any
one carbon atom are able to overlap equally well with the similar orbitals of both the carbon atoms on either sides. A
continuous ring of electron cloud covering all the six carbon atoms results because of such overlap. Since a 'p' orbital
consists of two equal lobes, one lying above and the other below the plane of the ring, the sideways overlapping of
the p orbitals in benzene molecule leads to a molecular orbital consisting to two continuous rings, one lying above,
and the other below the plane of the ring as shown.
The continuous rings of the p molecular orbital of benzene. One lying above and the other below the plane of the ring.
The shape and size of benzene molecule.
Thus, each bond in benzene has a character intermediate between a single and a double bond
What is a Tsunami?
The term "tsunami" describes a series of long oceanic waves that is created
in after a large volume of water has been displaced. “Tsunami” is derived
from the Japanese language, and when transcribed to English, it means
“Harbor (“tsu”) Wave (“nami”). The term was first coined by Japanese
fisherman to describe the destruction caused by large waves that would wipe
out entire areas surrounding the harbor. The strange thing was that they
would experience little to no effects of the tsunami on their boats in their
sea.
Tsunamis are waves characterized by moving at fast speeds,
sometimes having a high amplitude (wave height), and long
wavelength – thus tsunamis are essentially giant waves. In the
deep ocean, tsunamis are barely felt since they are masked by the
sheer vastness of the rest of the ocean. This is the reason why
those aforementioned Japanese fishermen were not affected.
However, tsunamis can be absolutely devastating as ocean’s depth
decreases with approaching land.
The speed at which a tsunami travels is another impressive

characteristic. Tsunamis can travel at great speeds across an ocean,
usually from 500 to 1000 kilometers per hour, with hardly any
energy losses and are barely noticeable out at sea. This is the
reason why tsunami’s generated from one region can affect other
regions thousands of kilometers away. With the recent tsunami is
South Asia, the epicenter of the tsunami was just of the coast of
Indonesia, and yet the tsunami struck with the same amount of
force in Eastern Africa – some 14 hours after Southeast Asia was
hit.
Wavelengths (the distance between wave crests) of tsunami can be in
excess of 100 kilometers or more. This means that once a tsunami initially
hits the coast, the second wave might not occur for up to an hour
afterwards. That is part of the inherent dangers of tsunamis. With the
recent tsunami in South Asia, many individuals were killed with the initial
wave. However, more tragedy struck when a second tsunami claimed just
as many people about an hour after the first tsunami, who had rushed back
onto the beach after to help out survivors.
As a tsunami leaves the deep water of the ocean and travels into the
shallower water near the coast, it behaves like a normal wave, only that it
travels significantly faster and packs more power with its long wavelength.
The tsunami slows down because of the shallow water, but that also makes
the water “pile up” to increase the tsunami’s height. By the time it reaches
land, the tsunami’s height can be horrifically imposing (some have been
known to be as high as 30 meters), and their effects can be equally
devastating as they batter the coast with tremendous amounts of energy.
Tsunamis can strip sand from beaches, tear up trees, and even obliterate
whole towns as seen with the latest South Asian tsunami disaster.
A more familiar term that is often used to describe tsunamis is “tidal wave”.
This was used since the violent onrushing of tsunamis can be seen as being
similar to a very large and fast tide. Oceanographers are quick to point out
that tidal wave is a misleading term that is incorrect in use because
tsunamis are not connected with tides in any way. Tides are the periodic
movement of water produced by the gravitational pull of the sun and moon,
whose entrance and exit can be accurately predicted. Tsunamis are a rare
phenomenon that is caused by the displacement of massive amounts of
water and manifest itself as a series of massive waves.

Drawbacks of Open Chain Structure

Uploaded by

Copyright:

Available Formats

Drawbacks of Open Chain Structure

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Drawbacks of Open Chain Structure

Uploaded by

Copyright:

Available Formats

The molecular formula of benzene has been found from analytical data, to be C6H6.

Relatively higher proportion of

Open Chain Structure

Drawbacks of open chain structure

These facts suggest a ring structure for benzene.

Ring structure of benzene

• The saturated nature of benzene.

Claus diagonal Dewar'sformula(1867) formula(1867)

Resonance hybrid structure of benzene

Evidences which support resonance structure of benzene

Large resonance energy

Orbital structure of benzene

• All carbon-carbon bond lengths are equal at 139 pm.

• All CC angles (or CH angles) are equal at 120°.

The speed at which a tsunami travels is another impressive

You might also like