Aromatic Chemistry: Structure of Benzene Ring, Nitration of Benzene, Friedel-Crafts Reactions

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The Benzene Ring

Benzene is a molecule that has the formula C6H6. The chemistry relating to it is called aromatic because many fragrant substances contain this structure. Benzene forms a rings as follows.

bonding in the benzene ring

The carbon atoms are bonded in a ring with a single hydrogen bonded to each. However, this means that each carbon only has 3 bonds. The fourth bond is the pi bond, which is delocalized in the ring. All of these delocalized electrons act like a glue which make the ring stable.

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The stability of benzene can be demonstrated by comparing the hydrogenation of cyclohexa-1,3,5-triene with benzene. We work this out by tripling the hydrogenation of cyclohexane. The results of this investigation are outlined in the diagram below.

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hydrogenation of cyclohexene and benzene enthalpies

If the enthalpy of hydrogenation of cyclohexa-1,3,5-triene is three times that of cyclohexene, then the enthalpy is -360kJ/mol. So the hydrogenation of benzene releases 152kJ less energy per mole to reach the same point, and hence it is more stable. The benzene molecule is susceptible to attack by electrophiles (i.e.. positively charged species). This results in an intermediate where the delocalized ring is disrupted, which then regenerates: resulting in a substitution reaction.

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Nitration of Benzene

the overall reaction for the nitration of benzene

The nitration of benzene has the above overall reaction. This process is important in producing amines and also explosives. An important feature to note is the generation of the electrophile, as the nitric acid does not directly react with the benzene, rather the ion: NO2+ does. This ion is generated by the reaction of nitric acid with the catalyst: sulphuric acid in the following reactions.

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equations for the generation of the electrophile in the nitration of benzene

The reaction of this electrophile with benzene is represented by the mechanism below. This is the same mechanism for any electrophilic substitution of benzene, you simply need to replace the nironium ion with the relevant electrophile.

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the mechanism for the nitration of benzene

Friedel-Crafts Reactions

The Friedel-Crafts alkylation and acylation are two reactions of electrophilic substitution of benzene that use an AlCl3 catalyst to generate an electrophile from either a haloalkane or acylhalogen. The mechanism with the electrophile is the same as shown above with nitronium; but the following occurs to generate this electrophile.

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RCl + AlCl3 ® CH3CH2+ + AlCl4- RCOCl + AlCl3 ® [RCO]+ + AlCl4-

The molecule ethylbenzene is required in the manufacture of polystyrene. However, using Chloroethane would be too expensive. So first of all, ethene is protonated with HCl in the following reaction.

CH2=CH2 + HCl ® CH3CH2+ + Cl-

The remaining chloride ion then reacts with the aluminium chloride catalyst to make an anion.

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Categories : Organic

Recent edits by: Taylor (ScienceAid Editor), SpellBot, Jamie (ScienceAid Editor)

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