A Manual of the Chemistry of the Carbon Compounds

222 THE CBEM18TBY OF
OF SUCCINIC ACID.
When succinic acid is heated with bromine and water in sealed
tubes, two substituted acids are simultaneously produced,
Monobromosiiccinic Acid forms colourless crystals readily soluble in
water. On boiling its solution witli silver oxide, malic acid is formed ?—
AgOH = CA(OH) { gj;gg + AgBr
Bibromosticdnie Add is sparingly soluble in cold water and crystallizes
from a hot solution in prisms, It is also formed by heating
succinyl chloride with bromine and decomposing the bibromosuccinic
chloride thus formed with water. When sodium bibromosuocinate is
boiled with water it yields add sodium nwnobromomalate;—
„„„,(CO.ONa , TTn - rTTtnmvvi COOH
CaH2Br21 1 c o 0Na + H8O = C8Ha(OH)Br j cc0 0 0Na
By boiling the free acid with silver oxide and water it is converted
into tartario acid t—
i{ gggg + AgaO + HaO - C2H2(OH),{ gg;gg + 2AgBr
ISOSCCCINIO ACID.
This isomeride of succinic acid has been obtained from a bromopropionio
acid (see Lactio Acid) by a reaction analogous to that by which
/3 bromopropionic acid has been transformed into suocinio acid, By
heating a bromopropionic acid with potassium cyanide it is converted
into a cyanopropionic acid, which, wlion boiled with potash solution,
yields isosucoinic or mcthyl-mabnic add •—
CHa
CH3
I I "
CH—CN + 2HjO = CH—CO.OH + NH3
(JO.OH CO.OH
It forms colourless crystals, being more freely soluble in water than
succinio acid; the solution of a neutral isosuccinate is not precipitated
by ferrio ohloride. It melts at 129°-5 and decomposes when
heated above this temperature into carbon dioxide and propionio
acid. This acid is therefore a much less stable compound than succinic
acid, the cause of this being that it contains two carboxyls
combined with the same carbon atom, In the chapter on +he constitution
of the carbon compounds it has already been pointed out that