Reaction Fittigs Synthesis of a Hydrocarbon

Exampi.f. Ethyl Benzene from Brombenzene and Bromethyl1 

The residue of sodium bromide and sodium remaining in the flask must be handled with extreme caution. Water must not be added to it, nor must it be thrown into the sink or waste-jars, nor allowed to stand a long time it is better to throw the flask, which 

Shake 200 grammes of commercial ether in a separating funnel with half its volume of water the latter is allowed to run off, and the operation repeated a second time with a fresh quantity of water, by which the alcohol is removed. The ether is dried by standing over calcium chloride, not too little, two hours. It is then filtered through a folded filter, and can now be used for the above reaction. 

Fittig s synthesis of the aromatic hydrocarbons is the analogue of Wurtz synthesis of the aliphatic hydrocarbons, e.g.  

The three isomeric bromtoluenes do not react with the same ease. While the p-bromtoluene gives a good yield of p-xylene, the o-com-pound does not give good results, and the m-compound generally forms no xylene- Two alkyl residues can also, in many cases, be introduced into a hydrocarbon simultaneously, e.g.  

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