Tollen s ammoniacal silver nitrate reagent

It is preferable to use Tollen s ammoniacal silver nitrate reagent, which is prepared as follows Dissolve 3 g. of silver nitrate in 30 ml. of water (solution A) and 3 g. of sodium hydroxide in 30 ml. of water (solution B). When the reagent is requir, mix equal volumes (say, 1 ml.) of solutions A and JB in a clean test-tube, and add dilute ammonia solution drop by drop until the silver oxide is just dissolved. Great care must be taken in the preparation and use of this reagent, which must not be heated. Only a small volume should be prepared just before use, any residue washed down the sink with a large quantity of water, and the test-tubes rinsed with dilute nitric acid. 

Thoria catalyst, 735 Tischenko reactions, 318 Tollen s ammoniacal silver nitrate reagent, 330, 1061, 1074 p-Tolualdehyde, 689, 697 o-Toluamide, 798 Toluene, 510, 516, 615 purification of, 173, 174 separation from benzene, 231 p-Toluenesulphinic acid, 821, 826 o-Toluenesulphonamide, 821, 824 p-Toluenesulphonamide, 820, 823 p-Toluenesulphonates, 422, 437, 650, 684 ... 

Ammoniacal silver nitrate solution (Totten s solution). Aldehydes alone reduce Tollen s reagent and produce a silver mirror on the inside of the test tube. Add 2-3 drops (or 0.05 g) of the compound to 2-3 ml of Tollen s solution contained in a clean test tube (the latter is preferably cleaned with hot nitric acid). If no reaction appears to take place in the cold, warm in a beaker of hot water. (CAUTION After the test, pour the contents of the test tube into the sink and wash the test tube with dilute nitric acid. Any silver fulminate present, which is highly explosive when dry, will thus be destroyed.)... 

Aldehydes are reductants. They are oxidized, for example, by the complex ion tetraiodomercurate-(n) (Nessler s reagent). The mercury of the complex is reduced to the metallic state. Aldehydes also reduce the ammoniacal silver nitrate (Tollens reagent) with the formation of metallic silver. Concerning this point, let s us recall that aldoses are also reductants. For example, they reduce cupric copper to cuprous copper (Fehling s reagent). Ketoses also exhibit this property. In this case, this is due to the presence of the group enediol in their structure. 

Nitro compounds and their reduction products. Tertiary nitro compounds (these are generally aromatic) are reduced by zinc and ammonium chloride solution to the corresponding hydroxylamines, which may be detected by their reducing action upon an ammoniacal solution of silver nitrate or Tollen s reagent ... 

The chemical properties of monosaccharides are further complicated by the fact that they can exhibit tautomerism in aqueous basic solutions (Figure 1.15). This means that after a short time a basic aqueous solution of a monosaccharide will also contain a mixture of monosaccharides that will exhibit their characteristic chemical properties. For example, a solution of fructose will produce a silver mirror when treated with an ammoniacal solution of silver nitrate (Tol-len s reagent). This is because under basic conditions fructose undergoes tautomerism to glucose, whose structure contains an aldehyde group, which reduces Tollen s reagent to metallic silver. 

Reducing action of dextrose silver mirror.—Test a dilute solution of glucose with an ammoniacal solution of silver nitrate or with Tollen s reagent (experiment 106d, page 84). 

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