udy of the product shows that the oxidation is not simple nor in
direct quantitative relationship to the H_{2}O_{2} employed. The
molecular proportion of the aldoses affected appears to be in
considerable excess, and the reaction is probably complicated by
interior rearrangement.

In the main, the original aldehydic group resists the oxidation. But a
certain proportion of acid products are formed, probably tartronic acid.
On distillation with condensing acids a large proportion of volatile
monobasic acids (chiefly formic) are obtained. The proportion of
furfural obtained amounts to 3-4 per cent. of the weight of the original
carbohydrate.

Since the general result of these oxidations is the substitution of an
OH group for an H atom, it was of interest to determine the behaviour of
furfural with the peroxide. The oxidation was carried out in dilute
aqueous solution of the aldehyde at 20 deg.-40 deg., using 2-3 mols. H_{2}O_{2}
per 1 mol. C_{5}H_{4}O_{2}. The main product is a hydroxyfurfural, which
was separated as a hydrazone. A small quantity of a monobasic acid was
formed, which was identified as a hydroxypyromucic acid. Both aldehyde
and acid appear to be the alpha beta derivatives. The aldehyde gives
very characteristic colour reactions with phloroglucinol and resorcinol
in presence of hydrochloric acid, which so closely resemble those of the
lignocelluloses that there is little doubt that these particular
reactions must be referred to the presence of the hydroxyfurfural as a
normal constituent.

The study of these oxidations was then extended to typical unsaturated
hydrocarbons--viz. acetylene and benzene. (4) From the former the main
product was acetic acid, but the attendant formation of traces of ethyl
alcohol indicates that the hydrogen of the peroxide may take a direct
part in this and other reactions. This view receives some support from
the fact that the interaction of the H_{2}O_{2} with permanganates has
now been established to be an oxidation of the H_{2} of the peroxide by
the permanganate oxidation, with liberation, therefore, of the O_{2} of
the peroxide as an unresolved molecule [Baeyer].

Benzene itself is also powerfully attacked by the peroxide when shaken
with a dilute solution in presence of iron salts. The products are
phenol and pyrocatechol, with some quantity of an amorphous product
probably formed by condensation of a quinone with the phenolic products
of reaction.

* *