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The silver mirror test

Demonstrations designed to capture the student's imagination, by Colin Baker of Bedford School. In this issue: the silver mirror test

Bernhard Christian Gottfried Tollens (1841-1918) was a German chemist whose name has been recognised through the silver mirror test using Tollens' reagent. He developed this test to differentiate between aldose and ketose sugars. Tollens' reagent is an alkaline solution of ammoniacal silver nitrate and is used to test for aldehydes. Silver ions in the presence of hydroxide ions come out of solution as a brown precipitate of silver(I) oxide, Ag2O(s). This precipitate dissolves in aqueous ammonia, forming the diamminesilver(I) ion, [Ag(NH3)2]+. Ketones do not react with Tollens' reagent. 2Ag+(aq) + 2OH-(aq) Ag2O(s) + H2O(l) 2[Ag(NH3)2]+(aq) + 2OH-(aq

Ag2O(s) + 4NH3(aq) + H2O(l)

Kit 4 g Glucose, C6H12O6; 150 cm3 0.1 mol dm-3 AgNO3; 10 cm3 Concentrated ammonia solution (0.88), NH3; 10 cm3 Distilled water; 250 cm3 Round bottom flask; One-litre beaker (water bath); 250 cm3 Beaker; and 50 cm3 beaker.

Within five minutes the inside of the flask should be coated with a highly reflective silver mirror.Mirror mirror in the flask who has a aldehyde in their solution? Procedure Dissolve 4 g of glucose in 10 cm3 distilled water in a 50 cm3 beaker. Some sources recommend that the glassware is scrupulously clean.88) to the silver nitrate solution while stirring. Concentrated solutions release ammonia vapour. which is hazardous if inhaled. Add 5 cm3 concentrated ammonia solution (0. Safety Silver nitrate is poisonous if swallowed or inhaled. Add the glucose solution to the ammoniacal silver nitrate solution in the beaker while stirring and then pour this mixture into a 250 cm3 round bottom flask. the solid/ solution stains (brown/black marks) the skin. which cannot be removed with soap and water but disappears as new skin grows. Ammonia contact with the eyes can cause long-term damage. Special tips Most recipes for this demonstration involve sodium hydroxide to provide alkaline conditions for the precipitation of silver(i) oxide. which produces silver in a more controlled manner. The solution is corrosive and may cause burns. A brown precipitate of silver oxide is formed which dissolves when a second 5 cm3 measure of concentrated ammonia solution is added.1 mol dm-3 silver nitrate in a 250 cm3 beaker. but I find that the temperature of the water bath is more important because the rate of deposition is the critical factor in a successful monstration. Teaching goals Adding the ammonia to the silver nitrate solution makes the silver ion less susceptible to reduction. I use concentrated ammonia solution which provides sufficient hydroxide ions to cause precipitation followed by the formation of the diamminesilver(i) ion. . Place this flask into a 70 oC water bath. Place 150 cm3 0.

eg Benedict's and Fehling's.4-dinitrophenylhydrazine dissolved in acidified methanol). and therefore will identify both aldehydes and ketones because both types of compound include a carbon-oxygen double bond. Basic conditions are necessary because glucose is oxidised more easily under basic conditions: RCHO + H2O RCOOH + 2H+ + 2e- Tollens' reagent and other similar tests.Ag+ + e- Ag E° = +0.373 V Ag(NH3)2+ + e- The half-equations indicate that ammonia forms a complex with the silver ion. will test for aldehydes but will not identify individual compounds. A bright orange or yellow precipitate will indicate the presence of aldehyde or ketone. If the precipitate is purified by recrystallisation. the silver ion is reduced so quickly that colloidal silver metal would appear.799 V Ag + 2NH3 E° = +0. which does not involve oxidation. The solution would become a black. then the unknown compound must be reacted with Brady's reagent (2. the melting point of the crystals can be measured and compared with tables of the melting points of 2. They all rely on aldehydes being susceptible to oxidation whereas ketones are not readily oxidised. cloudy liquid. If silver nitrate is used without ammonia. . This reaction is an example of addition-elimination. This is because silver ions form more stable complexes with NH3 than with water. If identification is required. which is more difficult to reduce than the silver ion.4-dinitrophenylhydra-zones of all the common aldehydes and ketones to identify the mystery compound.