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ISOMERS

Benzene

Description: Benzene is a clear liquid, volatile, colorless, highly flammable, odor característico.El most common commercial grade containing between 50 and 100% of Benzene.

Uses.

Benzene is used as a constituent of motor fuels, solvents, fats, oils, paints and nuts in the photo engraving prints. It is also used as a chemical intermediate.
Benzene is also used in the manufacture of detergents, explosives, pharmaceuticals and dyes.

A partial list of occupations at risk of exposure include

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  Burnishers.


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  Manufacturers carbolic acid.


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  Manufacturers maleic acid.


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  adhesives manufacturers.


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  Manufacturers of dry batteries.


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  Rubber Manufacturers.


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  Manufacturers of dyes.


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  Manufacturers of detergents.


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  styrene manufacturers.


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  Manufacturers benzene hexachloride.


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  linoleum manufacturers.


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  Manufacturers putty.


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  Manufacturers of nitrobenzene.


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  Manufacturers of adhesives.


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  impregnators asbestos products.


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  Chemicals.


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  Welders.


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  Furniture Finishers.


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  Workers with chlorobenzene.


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  petrochemical industry workers

Risks.
Route of Entry: Inhalation of vapor that can be supplemented by skin absorption, while the benzene is absorbed through healthy skin.

Adverse effects:

Local
. Exposure to liquid and vapor can cause primary irritation of the eyes, skin and upper respiratory tract. If the liquid gets into the lungs can cause pulmonary edema and hemorrhage. Following the removal of fat from the skin can produce etirema, blistering and dermatitis dry scarified. Systematic

. Acute exposure to benzene produces central nervous system depression. They can also cause headache, dizziness, nausea, vomiting, convulsions, coma and muerte.Se has shown that chronic exposure to benzene causes blood disorders. Benzene is myelotoxic agent

Caution.
permissible exposure limits: It is 1 ppm for a time-weighted average of 8 hours, with a peak of 5 ppm above the maximum acceptable for a maximum of 15 minutes.

Personal precautions: You should always use protective clothing. Wet clothing should be discarded deinmediato benzene. In areas where exposure is constant and should wear waterproof gloves to cover exposed body areas. In areas where splashing can be used mask or goggles. In areas where there are high concentrations of vapor is required to wear masks with organic vapor filter or "line of breath or breathing apparatus.

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disubstituted benzenes
There are only three possible isomers in any disubstituted benzene due to the planar symmetry of the ring, to identify these IUPAC nomenclature preferred to use the numbers 1.2, 1.3, 1.4 The system of prefixes is aplied widespread and is used when there disubstitution:

• ortho-, or o-isomer to 1.2
• meta-, or m-isomer to 1.3
• para-, or p-isomer to 1.4

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USES PHYSICAL AND CHEMICAL PROPERTIES OF BENZENE BENZENE

CHEMICAL PROPERTIES

aromatic substitution can follow three paths, electrophilic, nucleophilic and free radicals. Reactions aromatic substitution are most commonly caused by electrophilic reagents. Their ability to act as an electron donor due to the polarization of the benzene ring. Typical reactions of benzene are substitutes. Relief workers most frequently used are chlorine, bromine, nitric acid and hot concentrated sulfuric acid.

Halogenation

chlorine and bromine substitution derivatives are called aryl halides.
C6H5Cl C6H6 + Cl2 + HCl C6H6 + Br2 Chlorobenzene
C6H5Br + HBr bromobenzene

The halogenation is favored by low temperature and a catalyst such as iron or aluminum trichloride, which polarizes the halogen X  strongly to produce the reaction. The catalysts are usually substances that are deficient in electrons. Sulfonation

When benzene hydrocarbons are treated with fuming sulfuric acid (sulfuric acid containing sulfur trioxide) H2SO4 + SO3 form characteristic compounds that are known as sulfonic acids. In fact, it is believed that the active agent is SO3

C6H6 + + H2O C6H5SO3H HOSO3H benzene sulfonic acid

Nitration

fuming nitric acid or a mixture of nitric and sulfuric acids (nitrating mixture), a part of nitric acid and three sulfur produces Nitroderivatives , by substitution. Sulfuric acid absorbs the water produced in the nitration, and prevents the reverse reaction: C6H6 +

C6H5NO2 + H2O HONO2 Nitro-benzene

Combustion.

Benzene is flammable and burns with sooty flame, most characteristic property of aromatic compounds and is due to its high carbon content.

+15 2 C6H6 + O2 6H2O 12CO2

hydrogenation.
benzene ring by catalysis, fixed six hydrogen atoms, forming cyclohexane, thus maintaining the structure of the closed chain.

3H2 C6H6 + C6H12

Synthesis and Friedel Crafts Alkylation

Benzene reacts with alkyl halides in the presence of anhydrous aluminum chloride as a catalyst, forming counterparts.

C6H5CH3 + C6H6 + HCl CH3Cl Toluene

The attack on the benzene ring by the electrophilic CH3 ion is similar to that made by the Cl ion in the halogenation.

Wurtz Synthesis - Fitting.

A modification of the Wurtz of the aliphatic series. Homologues of benzene can be prepared by heating an ethereal solution of an alkyl halide and a method sodio.Este aryl has the advantage over the Friedel - Crafts, that we know the structure of the product and can easily enter long strings normal.

PROPERTIES PHYSICAL

aromatic series is characterized by great stability due to the multiple forms resonant very low reactivity presenta.Muestra addition reactions. Benzene is a flat molecule with a high degree of saturation which favors substitution reactions. It is a liquid less dense than water and slightly soluble in ella.Es very soluble in other hydrocarbons. Benzene is very toxic to man

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BY THE MOLECULAR ORBITAL THEORY OF RESONANCE

According to this theory, the carbon atoms of the benzene molecule are hybridized trigonal (sp2 orbital ) which agrees with bond angles 120 ° and the hexagon formula.

Two of the sp2 orbital of each carbon overlap with two of its neighbors to form the hexagonal ring. The third orbital sp2 are links to the respective hydrogen atom. All these links both carbon-carbon, as carbon-hydrogen are signa-type and illustrated in the figure below.

carbocycle part of the molecule of benzene, consists entirely of links signa.

But recoprdemos that the fourth electron trigonal hybridization of the carbon atom remains in the 2pz orbital , which has not perpendincular hibiridado and the plane of the hybrid orbitals. The following figure shows the system formed by the six orbital P.

A quarter of a valence electron of each carbon atom in benzene remains in the 2pz orbital

Thus, each carbon atom would be the ability to form a pi bond with its neighbor. But since there are two neighboring atoms, linking two alternatives, which are represented schematically in Figure 1 and can be considered as belonging to the two resonance structures of benzene.

Each carbon atom in benzene is possible to form pi bonds with one or other of its neighbors, which gives rise to two alternative structures.

Both forms can set with equal justification, that is, neither has primacy over the other. Since it is possible that this molecule simultaneously the two structures, what happens is that electornes P (six in total) together form a pi system that takes the form of a ring with two regions, and the other by Ensim below the plane of the links signa, as illustrated in Fig.

The p electron of benzene is forming a pi-type electronically tag, which is shaped like a ring with two localisé regions on both sides of the plane of the links signa.

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STRUCTURE OF BENZENE BENZENE

Relatively recent experimental facts indicate that the carbon-carbon distances in the benzene molecule are exactly the same, in contradiction with the Kekule formula showing single and double bonds, whose length is different, in fact we know the following values:

• simple carbon-carbon link: 154 pm (picometer)


• Carbon-Carbon Double bond: 133 pm


• carbon-carbon bonds in benzene: 139 pm
  

These and other experimental evidence led then to believe that the Kekulé formula is not accurate presentation of the molecule benzene.

This consideration is contemplated in the so-called theory of resonance. This theory suggests that the actual structure of benzene each carbon-carbon bond is neither simple nor double, but an intermediate type link.

In general, the theory of resonance applies to cases that can not be achieved for a compound estrucutural unique formula that agrees well with the experimental facts and with the conventions used to describe these formulas, (rule octet, for example)

The actual presentation of the molecule, it is considered as a hybrid of resoncancia between various structures, called estrucuturas or resonant taxpayers. The resonance between these forms taxpayers are indicated by an arrow with a head on both ends. Thus, for benzene (using simplified formulas), we have the following resonance situation (without highlighting the link diferenteslongitudes)

This can only be described as a hybrid of these structures which are illustrated in the figure by barrra models and spheres.

The real estrucutura benzene molecule is a hybrid between the two estrucutras contrubuynetes illustrated here.

anyway for the great majority of purposes forms just use a single taxpayer.

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the Kekule formula

The structure of benzene has been to extend studied. The experimental results indicate that the formula has the shape of regular hexagon, and the carbon atoms in its vertices and a hydrogen atom attached to each carbon. Have proposed various structural formulas to suit these facts, but the most widely accepted today is to propose, in 1865, the German chemist Friedrich August Kekulé (1829-1896), which is the formula presented earlier.