Brady's Tests Can Be Used To Qualitatively Detect The Carbonyl Functionality of A

Brady’s Tests can be used to qualitatively detect the carbonyl functionality of a
ketone or aldehyde functional group. A positive test is signaled by a yellow, orange or

red precipitate (known as a dinitrophenylhydrazone.) If the carbonyl compound is
aromatic, then the precipitate will be red; if aliphatic, then the precipitate will have a
more yellow color. The reaction between 2,4-Dinitrophenylhydrazine and a ketone is
shown below:
RR'C=O + C6H3(NO2)2NHNH2 → C6H3(NO2)2NHNCRR' + H2O
This reaction can be described as a condensation reaction, with two molecules

joining together with loss of water. It is also considered an addition-elimination reaction:
nucleophilic addition of the -NH2 group to the C=O carbonyl group, followed by the
removal of a H2O molecule.
Crystals of different hydrazones have characteristic melting and boiling points,

allowing the identity of a substance to be determined in a method known as
derivatization. In particular, the use of 2,4-dinitrophenylhydrazine was developed by
Brady and Elsmie. Modern spectroscopic and spectrometric techniques have since
superseded these techniques.
Dinitrophenylhydrazine does not react with other carbonyl-containing functional

groups such as carboxylic acids, amides, and esters. For carboxylic acids, amides and
esters, there is resonance associated stability as a lone-pair of electrons interacts with
the p-orbital of the carbonyl carbon resulting in increased delocalization in the molecule.
This stability would be lost by addition of a reagent to the carbonyl group. Hence, these
compounds are more resistant to addition reactions. Also with carboxylic acids there is
the effect of the compound acting as a base, leaving the resulting carboxylate
negatively charged hence unable to be attacked by this nucleophile.
Fehling's test differentiates between aldehydes and ketones. Aldehydes can be
oxidized by Cu2+ in the presence of a strong base to form carbonic acids. Ketones
cannot be oxidized by this reaction. When the Cu2+ oxidizes the aldehydes it is reduced
to Cu+, and forms the compound Cu2O, which is a reddish precipitate. That is how you
know you have an aldehyde.
Fehling's reagent is usually formed by mixing CuSO4, sodium citrate, and sodium
carbonate. The carbonte is used to raise the pH, but doing so would normally form
Cu(OH)2, a precipitate. That is where the sodium citrate comes it---the citrate
complexes the Cu2+ ions and prevents them from precipitating.
Tollens' reagent is a chemical reagent most commonly used to determine

whether a known carbonyl-containing compound is an aldehyde or a ketone. It is usually
ammoniacal silver nitrate, but can also be other mixtures, as long aqueous
diamminesilver(I) complex is present.
A positive test with Tollens' reagent results in elemental silver precipitating out of
solution, occasionally onto the inner surface of the reaction vessel, producing a
characteristic and memorable "silver mirror" on the inner vessel surface.
Aldehydes will be positive in Tollen's test and a mirror-like material will be

formed.Tollens' reagent can be used to determine whether the compound is a ketone or
an aldehyde. Importantly, there is a special case in which Tollens' reagent will give a
positive for a ketone; if the ketone is an alpha-hydroxy ketone, then the Tollens' reagent
will react.
The test rests on the premise that aldehydes are more readily oxidised compared
with ketones; this is due to the carbonyl-containing carbon in aldehydes having an
attached hydrogen. The diamminesilver(I) complex in the mixture is an oxidizing agent
and is the essential reactant in Tollens' reagent. The test is generally carried out in a
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 acidification will give its corresponding carboxylic acid. The carboxylic acid is not
directly formed in the first place as the reaction takes place under alkaline conditions.
The ionic equations for the overall reaction are shown below; R refers to analkyl group.
[2]
[Ag(NH3)2]+ (aq) + e- → Ag (s) + 2 NH3 (aq)
RCHO (aq) + 3 OH- → RCOO- + 2 H2O + 2 e-
The negative result for the test is no precipitate of silver formed when the
carbonyl to be tested is added. A ketone will give a negative result because it cannot be
oxidized easily. A ketone has no available hydrogen atom attached to the carbonyl
carbon, meaning it can't be so easily oxidized - unlike an aldehyde, which has this
hydrogen atom.
Tollens' reagent is also a test for alkynes with a triple bond in the 1-position. A
yellow precipitate of the metal acetylide is formed in this case.Both Tollens' reagent and
Fehling's reagent also give positive results with formic acid (methanoic acid - HCOOH),
which is fully oxidised to water and carbon dioxide.
In anatomic pathology, ammoniacal silver nitrate is used in the Fontana-Masson

Stain, which is a silver stain technique used to detect melanin, argentaffin and lipofuscin
in tissue sections. Melanin and the other.
The Schiff test is a chemical test for the detection of aldehydes.[2] An unknown

sample is added to the decolorized Schiff reagent and when aldehyde is present a
characteristic magenta or purple color develops.
The reaction of the Schiff reagent with aldehydes is complex with several
research groups reporting multiple reaction products with model compounds. Two
different mechanisms appear in the literature [3] The first mechanism explaining its
action with aldehydes was proposed by H. Wieland in 1935. In it the aldehyde groups
react with the sulfinic acid groups forming an sulfonamide.
chromaffins reduce the silver nitrate to metallic silver.

Iodoform is the organoiodine compound with the formula CHI3. A pale yellow,
crystalline, volatile substance, it has a penetrating odor (in older chemistry texts, the
smell is sometimes referred to as the smell of hospitals) and, analogous to chloroform,
sweetish taste. It is occasionally used as a disinfectant. It is also known as tri-
iodomethane, and sometimes also referred to as carbon triiodide (which is not strictly
correct, as this compound also contains hydrogen) or methyl triiodide (which is
somewhat ambiguous as that name could also refer to the methylated triiodide ion,
CH3I3).
It is synthesized in the haloform reaction by the reaction of iodine and sodium

hydroxide with any one of these four kinds of organic compounds:
(i) a methyl ketone:
CH3COR, acetaldehyde (CH3CHO), ethanol (CH3CH2OH), and certain

secondary alcohols (CH3CHROH, where R is an alkyl or aryl group).
The reaction of iodine and base with methyl ketones is so reliable, that the

"iodoform test" (the appearance of a yellow precipitate) is used to probe the presence of
a methyl ketone. This is also the case when testing for secondary alcohols (methyl
alcohols).
Some reagents ( Hydrogen iodide) convert iodoform to diiodomethane. Also

conversion to carbon dioxide is possible: Iodoform reacts with aqueoussilver nitrate to
produce carbon monoxide, which is oxidized by mixture of sulfuric acid and iodine
pentaoxide. When treated with powdered elemental silver the iodoform is reduced,
producing acetylene. Upon heating iodoform decomposes to produce diatomic iodine,
hydrogen iodide gas, and carbon.
CONCLUSION
From the experiment, the Unknown give the negative result to Brady’s Test, Tollen’s
Test ,Fehling’s Test and give the positive result to Iodoform Test.SO we can conclude
that Unknown is Ketone.

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Brady’s Tests can be used to qualitatively detect the carbonyl functionality of a

ketone or aldehyde functional group. A positive test is signaled by a yellow, orange or

RR'C=O + C6H3(NO2)2NHNH2 → C6H3(NO2)2NHNCRR' + H2O

This reaction can be described as a condensation reaction, with two molecules

Crystals of different hydrazones have characteristic melting and boiling points,

Dinitrophenylhydrazine does not react with other carbonyl-containing functional

Tollens' reagent is a chemical reagent most commonly used to determine

Aldehydes will be positive in Tollen's test and a mirror-like material will be

[Ag(NH3)2]+ (aq) + e- → Ag (s) + 2 NH3 (aq)

RCHO (aq) + 3 OH- → RCOO- + 2 H2O + 2 e-

In anatomic pathology, ammoniacal silver nitrate is used in the Fontana-Masson

The Schiff test is a chemical test for the detection of aldehydes.[2] An unknown

chromaffins reduce the silver nitrate to metallic silver.

It is synthesized in the haloform reaction by the reaction of iodine and sodium

CH3COR, acetaldehyde (CH3CHO), ethanol (CH3CH2OH), and certain

The reaction of iodine and base with methyl ketones is so reliable, that the

Some reagents ( Hydrogen iodide) convert iodoform to diiodomethane. Also

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