82 
Proceedings of the Boycd Society 
5. On the Oxidation of Phenyl Alcohol, and a Mechanical 
Arrangement adapted to illustrate Structure in the Non- 
saturated Hydrocarbons. By J. Dewar, Esq. Communi- 
cated by Professor Playfair. 
The syntheses and oxidation analyses of organic compounds 
have so confirmed each other in many cases, that chemists are 
enabled to judge of the structure of a compound from the oxidation 
products. Many chemists have used the oxidation method in 
special cases, the bodies operated upon belonging principally to 
the fatty series ; but until Fittig and Beilstein published their 
memoirs on the aromatic compounds, it was never applied to the 
systematic study of a hydrocarbon and its derivatives. But al- 
though the syntheses and oxidation analyses of the derivatives of 
benzol confirmed each other, still the structure of the original 
nucleus (benzol) remained unexplained. Kekule’s original and 
elegant speculations on the structure of benzol and its derivatives 
induced me to try the effect of oxidising agents on benzol, with 
the view of eliciting whether the carbon atoms would separate in 
the way theory pointed out. The carbon atoms in benzol may be 
supposed to be arranged in a closed chain, where the carbon affini- 
ties are bound two and one alternately. Now, if we examine the 
formula graphically, it is evident there are three symmetrical 
groupings, C 2 H 2 (acetylene), in benzol. We would, therefore, ex- 
pect the carbons to separate in twos, and produce the corresponding 
oxidised product, C 2 H 2 0 4 , oxalic acid. I attempted the oxidation 
of benzol with permanganate of potash, but no decomposition took 
place in a sealed tube at 150° C. I then had recourse to phenyl 
alcohol. If a solution of permanganate of potash is added to 
phenyl alcohol, dissolved in water, the decomposition is immediate, 
the solution becomes alkaline, and peroxide of manganese separates 
as a bulky precipitate. Equivalent quantities of the substances, 
1 pt. phenyl alcohol to 3‘5 pts. of permanganate of potash were the 
proportions used. If the liquid is filtered and acidulated with 
acetic acid, on the addition of acetate of lime, a white precipitate 
of oxalate of lime separates. I have analysed the lime salt, and 
also examined the physical properties of the acid. So that phenyl 
