Tollens reagent

2 AgNO3 + 2 NaOH Ag2 O (s) + 2 NaNO3

+ H2 O
In the next step, sucient aqueous ammonia is added to
dissolve the brown silver(I) oxide. The resulting solution contains the [Ag(NH3 )2 ]+ complexes in the mixture,
which is the main component of Tollens reagent. Sodium
hydroxide is reformed:
Ag2 O (s) + 4 NH3 + 2 NaNO3 + H2 O 2
[Ag(NH3 )2 ]NO3 + 2 NaOH
Alternatively, aqueous ammonia can be added directly to
silver nitrate solution.[1] At rst, ammonia will induce formation of solid silver oxide, but with additional ammonia, this solid precipitate dissolves to give a clear solution
of diamminesilver(I) complex ( [Ag(NH3 )2 ]+ ). Filtering
the reagent before use helps to prevent false-positive results.

Tollens test for aldehyde: left side positive (silver mirror), right
side negative

2 Uses
2.1 Qualitative organic analysis
Once the presence of carbonyl group has been identied
using 2,4-dinitrophenylhydrazine (also known as Bradys
reagent or 2,4-DNPH), Tollens reagent can be used to
distinguish ketone vs aldehyde. Tollens reagent gives a
Ball-and-stick model of the diamminesilver(I) complex
negative test for most ketones, except those with alphaTollens reagent is a chemical reagent used to determine hydroxy ketone.
the presence of an aldehyde or alpha-hydroxy ketone The test rests on the premise that aldehydes are more
functional groups. The reagent consists of a solution of readily oxidised compared with ketones; this is due to
silver nitrate and ammonia. It was named after its discov- the carbonyl-containing carbon in aldehydes having an aterer, the German chemist Bernhard Tollens. A positive tached hydrogen. The diamminesilver(I) complex in the
test with Tollens reagent is indicated by the precipitation mixture is an oxidizing agent and is the essential reactant
of elemental silver, often producing a characteristic sil- in Tollens reagent. The test is generally carried out in a
ver mirror on the inner surface of the reaction vessel.
test tube in a warm water bath.

In a positive test, the diamminesilver(I) complex oxidizes

the aldehyde to a carboxylate ion and in the process is
reduced to elemental silver and aqueous ammonia. The
elemental silver precipitates out of solution, occasionally
onto the inner surface of the reaction vessel, giving a characteristic silver mirror. The carboxylate ion on acidication will give its corresponding carboxylic acid. The
carboxylic acid is not directly formed in the rst place as
the reaction takes place under alkaline conditions. The
ionic equations for the overall reaction are shown below;
R refers to an alkyl group.[2]

Laboratory preparation

This reagent is not commercially available due to its short

shelf life. It must be freshly prepared in the laboratory.
One common preparation involves two steps. First a
few drops of dilute sodium hydroxide are added to some
aqueous silver nitrate. The OH ions convert the silver
aquo complex form into silver oxide, Ag2 O, which precipitate from the solution as a brown solid:
1

6
2 [Ag(NH3 )2 ]+ + RCHO + H2 O 2 Ag(s) +
4 NH3 + RCO2 H + 2 H+

Tollens reagent can also be used to test for terminal

alkynes (RC2 H). A yellow precipitate of the acetylide
(AgC2 R) is formed in this case. Another test relies on
reaction of the furfural with phloroglucinol to produce a
colored compound with high molar absorptivity.[3]
Both Tollens reagent and Fehlings reagent also give positive results with formic acid, which is fully oxidised to
water and carbon dioxide.

2.2

Staining

In anatomic pathology, ammoniacal silver nitrate is used

in the Fontana-Masson Stain, which is a silver stain technique used to detect melanin, argentan and lipofuscin in
tissue sections. Melanin and the other chromans reduce
the silver nitrate to metallic silver.[1]

2.3

In silver mirroring

Tollens reagent is also used to apply a silver mirror to

glassware; for example the inside of an insulated vacuum
ask. The reducing agent is glucose (an aldehyde) for
such applications. Clean glassware is required for a high
quality mirror. To increase the speed of deposition the
glass surface may be pre-treated with tin(II) chloride stabilised in hydrochloric acid solution.[4]
For applications requiring the highest optical quality such
as in telescope mirrors the use of tin(II) chloride is problematic, since it creates nanoscale roughness and reduces
the reectivity.[5] [6] Methods to produce telescope mirrors include additional additives to increase adhesion and
lm resilience, such as in Martins Method, which includes tartaric acid and ethanol.[6]

Safety

Aged reagent can be destroyed with dilute acid to prevent

the formation of the highly explosive silver nitride.[7]

See also
Bradys reagent
Benedicts reagent
Fehlings solution
Walden reductor (opposite use involving metallic
silver)

EXTERNAL LINKS

5 References
[1] Webpath website http://library.med.utah.edu/WebPath/
HISTHTML/MANUALS/FONTANA.PDF Accessed 4
February 2009
[2] http://www.chemguide.co.uk/organicprops/carbonyls/
oxidation.html Accessed 31 January 2010
[3] Oshitna, K., and Tollens, B., Ueber Spectral-reactionen
des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425
(1901)
[4] Hart, M. (1992). Manual of scientic glassblowing. St.
Helens, Merseyside [England]: British Society of Scientic Glassblowers. ISBN 0-9518216-0-1.
[5] N. Chitvoranund1; S. Jiemsirilers; D.P. Kashima (2013).
Eects of surface treatments on adhesion of silver lm on
glass substrate fabricated by electroless plating. Journal
of the Australian Ceramic Society 49: 62 69.
[6] C. Heber D. (Feb 1911). Methods of Silvering Mirrors.
Publications of the Astronomical Society of the Pacic 23
(135): 1519.
[7] Svehla, G.; Vogel, Arthur Anton (1996). Vogels qualitative inorganic analysis. New York: Longman. ISBN
0-582-21866-7.

6 External links
Video of experimental process involving Tollens
reagent
Tollens reagent on www.wiu.edu
Univ. of Minnesota Organic Chemistry Class Demo
Result

Text and image sources, contributors, and licenses

7.1

Text

Tollens reagent Source: https://en.wikipedia.org/wiki/Tollens{}_reagent?oldid=664929191 Contributors: Stone, Mervyn, Centrx,

Tom harrison, Jlm255, Chiu frederick, MeltBanana, Spinal83, Reinyday, Enric Naval, Benjah-bmm27, Mailer diablo, EachyJ, V8rik,
Crocodealer, Physchim62, YurikBot, Tony1, Alchie1, Robert L, Itub, Asht0n, SmackBot, MattieTK, Edgar181, Sbharris, Shalom Yechiel,
Chlewbot, Smokefoot, Peterwhy, Mattopaedia, Dr. Sunglasses, Syrcatbot, Beetstra, Menswear, Rieman 82, Nonagonal Spider, Escarbot,
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7.2

Images

File:Diamminesilver(I)$-$3D-balls.png Source:
https://upload.wikimedia.org/wikipedia/commons/a/a6/Diamminesilver%28I%
29-3D-balls.png License: Public domain Contributors: Own work Original artist: Benjah-bmm27
File:Tollens.JPG Source: https://upload.wikimedia.org/wikipedia/commons/5/52/Tollens.JPG License: Public domain Contributors: Own
work Original artist: FK1954

7.3

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