PHTHALIC 

ACID Sodium amalgam (cold) Alkali A 2'e DIHYDRO < Hydrobromide with ll alcoholic potash A 2.4 DIHYDRO I Anhydride with acetic anhydride Sodium amalgam ± acetic acid ( A3.5 DIHYDRO (TRANS.) {\/` Acetic anhydride 43.5 DIHYDRO (CIS.) A 1.4 D11:MR0 Sodium amalgam Boil with water suberyl bromide . Cyclo-heptene, C7H12, is obtained by the action of alcoholic potash on suberyl iodide; and from cyclo-heptane carboxylic acid, the amide of which by the action of sodium hypobromite is converted into cyclo-heptanamine, which, in its turn, is destructively methylated (R . Willstatter, Ber., 1901, 34, 131) . Cyclo-heptadiene 1.3, C7H15, is obtained from cyclo-heptene (Willstatter, loc. cit.) . It is identical with the hydrotropilidine, which results by the destructive methylation of tropane . Euterpene (trimethyl-I.4.4-cyclo-heptadiene I.5), C10Ha5 is prepared from dihydroeucarveol . By the action of hydrobromic acid (in glacial acetic acid solution) and reduction of the resulting product it yields 1.2-dimethyl-4-ethylbenzene (A. v . Baeyer, Ber., 1897, 30, p . 2075) . Cyclo-heptatriene (tropilidine), C,H8, is formed on distilling tropine with baryta; and from cyclo-heptadiene by forming its addition product with bromine and heating this with quinoline to 150—16o° C . (R . Willstatter, loc. cit.) .

Chromic acid oxidizes it to benzoic acid and

benzaldehyde . With bromine it forms a di-bromide, which then heated to i io° C. decomposes into hydro-bromic acid and benzyl bromide . Cyclo-keptanol, CIH130H, is formed by the reduction of suberone, and by the action of silver nitrite on the hydrochloride of cyclohexanamine (N . I)emjanow, Centralblatt, 1904, i. p . 1214) . Cyclo-heptanone (suberone), C,H,20, is formed on the distillation of suberic acid with lime, and from a-brom-cyclo-heptane carboxylic acid by treatment with baryta and subsequent distillation over lead peroxide (R . Willstatter, Ber .. 1898, 31, p . 2507) . It is a colourless liquid having a peppermint odour, and boiling at 178.5–179.5° C . Nitric acid oxidizes it to n-pimelic acid . ( A2.5 DmvDRo Boil with water A1.5 DIHYDRO I Sodium amalgam Boil + NaOH A2 TETRAAIIYDRO A 1 TETRAHYDRO Dibromide on Hydrobromide Reduce alcoholic potash on reduction Remove H Br from A 1'3 DIHYDRO dibromide Cyclo-heptane Group .

Cyclo-heptane (suberane), C7H14, obtained by the reduction of suberyl iodide, is a liquid which boils at 117° C . On treatment with bromine in the presence of

aluminium bromide it gives chiefly pentabromtoluene . When heated with hydriodic acid to 230 C. it gives methylhexamethylene . On oxidation with nitric acid (sp. gr . 1.4) it yields pimelic acid .