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Encyclopedia Britannica



RCN

This article appears in Volume V15, Page 762 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: RAY-RHU
RCN + R'MgI - RR'C:NMgl RCOR'+ NH3+MgLOH.
The ketones are of neutral reaction, the lower members of the
series
  being colourless, volatile, pleasant-smelling liquids. They do not reduce silver solutions, and are not so readily oxidized as the aldehydes. On oxidation, the molecule is split at the carbonyl group and a mixture of acids is obtained. Sodium amalgam reduces them to secondary alcohols; phosphorus pentachloride replaces the carbonyl oxygen by chlorine, forming the ketone chlorides. Only those ketones which contain a methyl group are capable of forming crystalline addition compounds with the alkaline bisulphites (F. Grimm, Ann., 1871, 157, p. 262). They combine with hydrocyanic acid to form nitriles, which on
hydrolysis
  furnish hydroxyacids,
(CH3)2CO --> (CH3)2COHCN -> (CH3)2COHCO2H; with phenylhydrazine they yield hydrazones; with hydrazine they yield in addition ketazines RR'C:NN:CRR' (T. Curtius), and with
hydroxylamine
  ketoximes. The latter readily under-go the " Beckmann " transformation on treatment with acid chlorides, yielding substituted acid amides,
RR'.C:NOH --> RC(NR')OH -~ R.CO.NHR'
(see
OxIMES
 , also A. Hantzsch, Ber.,1891,24, p. 13). The ketones
react with mercaptan to form mercaptols (E. Baumann, Ber.,
1885, 18, p. 883), and with concentrated nitric acid they yield
dinitroparaffins (G. Chancel,
Bull
 . de la soc. chim., 1879, 31,
p. 503). With nitrous acid (obtained from amyl nitrite and
gaseous hydrochloric acid, the ketone being dissolved in acetic
acid) they form isonitroso-ketones, RCOCH:NOH (L. Claisen,
Ber., 1887, 20, pp. 656, 2194). With ammonia they yield
complex condensation products;
acetone
  forming di- and tri-
acetonamines (W. Heintz, Ann. 1875, 178, p. 305; 1877, 189,
p. 214. They also condense with aldehydes, under the influence
of alkalis or sodium ethylate (L. Claisen, Ann., 1883, 218, pp. 121,
129, 145; 1884, 223, p. 137; S. Kostanecki and G. Rossbach,
Ber., 1896, 29, pp. 1488, 1495, 1893, &c.). On treatment with the Grignard reagent, in absolute ether solution, they yield addition products which are decomposed by water with production of tertiary alcohols (V. Grignard, Comptes rendus, 1900,
130, p. 1322 et seq.),
RR'CO-3 RR'C(OMgI)R"-) RR'R"C(OH) + MgLOH. Ketones do not polymerize in the same way as aldehydes, but under the influence of acids and bases yield condensation products; thus
acetone
  gives mesityl
oxide
 , phorone and mesitylene (see below). _
For dimethyl ketone or acetone, see ACETONE. Diethyl ketone, (
C2H6
 )2CO, is a pleasant-smelling liquid boiling at 102.7 C. With concentrated nitric acid it forms dinitroethane, and it is oxidized by chromic acid to acetic and propionic acids. Methylnonylketone, CH3COC9H19, is the
chief
  constituent of oil of rue, which also contains methylheptylketone, CH3COC7 H15, a liquid of boiling-point 85-90 C. (7 mm.), which yields normal caprylic acid on oxidation with hypobromites.
Mesatyl
oxide
 , (CH3)2C:CHCOCH3, is an aromatic smelling liquid of boiling point 129.5-130 C. It is insoluble in water, but readily dissolves in alcohol. On
heating
  with dilute sulphuric acid it yields acetone, but with the concentrated acid it gives mesitylene, C9Hi2-Potassium permanganate oxidizes it to acetic acid and hydroxyisobutyric acid (A. Pinner, Ber., 1882, 15, p. 591). It forms hydroxyhydrocollidine when heated with acetamide and anhydrous zinc chloride (F. Canzoneri and G. Spica, Gam chim. Ital., 1884, 14, P349) Phorone,(CH3)2C:CHCOCH:C(CH3)2,formsyellow crystals which melt at 28 C. and boil at 197.2 C. When heated with phosphorus pentoxide it yields acetone, water and some pseudocumene. Dilute nitric acid oxidizes it to acetic and oxalic acids, while potassium permanganate oxidizes it to acetone, carbon dioxide and oxalic acid.


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