Benzene ring Hydrocarbons

The free radical mechanism is confirmed by the fact that if a substituted aromatic hydrocarbon is used in this reaction, the incoming group (derived from the diazotate) may not necessarily occupy the position in the benzene ring normally determined by the substituent present—a characteristic of free radical reactions. 

Members of a class of arenes called polycyclic aromatic hydrocarbons possess subslanlial resonance energies because each is a colleclion of benzene rings fused logelher... 

Polycyclic aromatic hydrocarbons, of which anthracene is an example contain two or more benzene rings fused together... 

Polyamine (Section 22 4) A compound that contains many ammo groups The term is usually applied to a group of nat urally occurring substances including spermine spermi dine and putrescme that are believed to be involved in cell differentiation and proliferation Polycyclic aromatic hydrocarbon (Section 118) An aromatic hydrocarbon charactenzed by the presence of two or more fused benzene rings... 

Being a hydrocarbon with a solubility parameter of 18.6MPa - it is dissolved by a number of hydrocarbons with similar solubility parameters, such as benzene and toluene. The presence of a benzene ring results in polystyrene having greater reactivity than polyethylene. Characteristic reactions of a phenyl group such as chlorination, hydrogenation, nitration and sulphonation can all be performed with... 

The polycyclic aromatic hydrocarbons such as naphthalene, anthracene, and phenan-threne undergo electrophilic aromatic substitution and are generally more reactive than benzene. One reason is that the activation energy for formation of the c-complex is lower than for benzene because more of the initial resonance stabilization is retained in intermediates that have a fused benzene ring. 

The aromatic hydrocarbons are used mainly as solvents and as feedstock chemicals for chemical processes that produce other valuable chemicals. With regard to cyclical hydrocarbons, the aromatic hydrocarbons are the only compounds discussed. These compounds all have the six-carbon benzene ring as a base, but there are also three-, four-, five-, and seven-carbon rings. These materials will be considered as we examine their occurrence as hazardous materials. After the alkanes, the aromatics are the next most common chemicals shipped and used in commerce. The short-chain olefins (alkenes) such as ethylene and propylene may be shipped in larger quantities because of their use as monomers, but for sheer numbers of different compounds, the aromatics will surpass even the alkanes in number, although not in volume. 

Polycyclic aromatic hydrocarbon (Section 11.8) An aromatic hydrocarbon characterized by the presence of two or more fused benzene rings. 

Benzene derivatives. Tbe nomenclature is a combination of the lUPAC system and traditional names. Many of the derivatives are named by the substituent group appearing as the prefbt. These may be considered a subclass of the aliphatic-aromatic hydrocarbon family, which contains both aliphatic and aromatic units in its structures. Thus, alkylbenzenes are made up of a benzene ring and alkane units alkenylbenzenes are Composed of a benzene ring and alkene units and alkynylbenzenes comprise a benzene ring and alkyne units. Examples of alkylbenzenes include... 

Polynuclear aromatic hydrocarbons. These consist of a variety of complex structures made up of aromatic rings alone, or combinations of aliphatic rings, aromatic rings, and aliphatic chains, etc. One such class of compounds is biphenyl and its derivatives, in which two benzene rings are connected by a single C — C linkage. The structural formula of biphenyl (or phenylbenzene) is... 

Although many of the aromatic compounds based on benzene have pleasant odors, they are usually toxic, and some are carcinogenic. Volatile aromatic hydrocarbons are highly flammable and burn with a luminous, sooty flame. The effects of molecular size (in simple arenes as well as in substituted aromatics) and of molecular symmetry (e.g., xylene isomers) are noticeable in physical properties [48, p. 212 49, p. 375 50, p. 41]. Since the hybrid bonds of benzene rings are as stable as the single bonds in alkanes, aromatic compounds can participate in chemical reactions without disrupting the ring structure. 

It may also be represented as a hexagon with a circle in the middle. The circle is a symbol of the n cloud encircling the benzene ring. The delocalized electrons associated with the benzene ring impart very special properties to aromatic hydrocarbons. They have chemical properties of single-bond compounds such as paraffin hydrocarbons and doublebond compounds such as olefins, as well as many properties of their own. 

In another type of aromatic hydrocarbon, two or more benzene rings are fused together. Naphthalene is the simplest compound of this type. Fusion of three benzene rings gives two different isomers, anthracene and phenanthrene. 

The application of these methods to unsaturated hydrocarbons involves certain complications. Unsaturated hydrocarbons show an additional polarizability19 of 0.58 x 10 24 cm3 per double bond and 0.86 x 10 24 cm3 per triple bond in the molecule. Similarly the polarizability of a molecule containing a benzene ring exceeds that computed for the atoms present by about 1.28 x 10 24 cm3. These results are most readily explained on the basis that oscillations of charge from atom to atom are significant when double bonds are present. 

In fused ring systems, the positions are not equivalent and there is usually a preferred orientation even in the unsubstituted hydrocarbon. The preferred positions may often by predicted as for benzene rings. Thus it is possible to draw more canonical forms for the arenium ion when naphthalene is attacked at the a position than when it is attacked at the p position, and the a position is the preferred site of attack,though, as previously mentioned (p. 682), the isomer formed by substitution at the p position is thermodynamically more stable and is the product if the reaction is reversible and equilibrium is reached. Because of the more extensive delocalization of charges in the corresponding arenium ions, naphthalene is more reactive than benzene and substitution is faster at both positions. Similarly, anthracene, phenanthrene, and other fused polycyclic aromatic hydrocarbons are also substituted faster than benzene. 

Steric influences are important in some cases. In catalytic hydrogenation, where the substrate must be adsorbed onto the catalyst surface, the reaction becomes more difficult with increasing substitution. The hydrocarbon 21, in which the double bond is entombed between the benzene rings, does not react with Br2, H2SO4, O3, BH3, CBr2, or other reagents that react with most double bonds. A similarly inactive... 

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