Online Encyclopedia

C6H5CHO

Online Encyclopedia
Originally appearing in Volume V01, Page 532 of the 1911 Encyclopedia Britannica.
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C6H5CHO  . The

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aldehydes are characterized`by their
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great chemical re-activity . They act as reducing agents,
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silver nitrate in the presence of
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ammonia being rapidly reduced to the condition of metallic silver . They are easily oxidized to the corresponding fatty acid, in many cases simply by exposure to air . Nascent hydrogen reduces them to
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primary alcohols, and phosphorus pentachloride replaces the carbonyl oxygen by chlorine . They form many addition compounds, combining with ammonia to form aldehyde ammonia s of the type R•CH(OH)•NH, . . These are colourless crystalline compounds, which are most readily prepared by passing ammonia
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gas into an ethereal solution of the aldehyde . With sodium bisulphite they form the so-called bisulphite compounds R•CH(OH)•SO3Na, which are readily resolved into their components by distillation with dilute acids, and are frequently used for the preparation of the pure aldehyde . With hydrocyanic acid aldehydes form the cyanhydrins R•CH(OH)•CN . They react with hydroxylamine and phenylhydrazine, with the formation of aldoximes and hydra-zones . (For the
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isomerism of the aldoximes see
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OXIMES) . The hydrazones are crystalline substances which are of value in the characterization of the aldehydes .

Both oximes and hydrazones, on boiling with dilute acid, regenerate the

parent aldehyde . The hydrazones are best prepared by mixing the aldehyde with phenylhydrazine in dilute acetic acid solution, in the absence of any
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free
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mineral acid . Semioxainazid, NH2•CO•CO•NH•NH2, has also been employed for the identification of aldehydes (W . Kerp and K . Unger, Berichte, 1897, 30. p . 585)• Aldehydes are converted into resins by the
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action of caustic alkalies . On
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heating with alcohols to loo° C. they form acetals, and they also form condensation products with para-amido-di-methyl-aniline (A . Cahn, Berichte, 1884, 17, p . 2939) . They react with the
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zinc alkyls to form addition products, which are decomposed by
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water with formation of secondary alcohols (K . Thurnlach, Ainalen, 1882, 213, p . 369) thus: Zn(
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C2H3)z H2O CH3•CHO CH3•CHCO2ZnC2H6
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CH3-CH<OH 3--ZnO+
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C2H6 .

The reaction is a

general one for all aldehydes with zinc methyl and zinc
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ethyl, but not with the higher zinc alkyls . V . Grignard (Comptes Rendus, 1900 et seq.) showed that aldehydes combine with magnesium alkyl iodides (in absolute ether solution) to form addition products, which are decomposed by water with the OC<RI+Cl •
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CH2 . COOC2H5- 0 formation of secondary alcohols, thus from acetaldehyde and magnesium methyl iodide, isopropyl
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alcohol is obtained .

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