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Tollen's reagent is a mild oxidizing agent used to detect aldehydes, resulting in a color change due to the reduction of silver ions to metallic silver. The document outlines various tests for carbonyl compounds, including the sodium bisulphite test, Fehling's solution test, and Schiff's reagent test, each confirming the presence of aldehydes or ketones through observable reactions. Additionally, the document describes the preparation and observations for each test, highlighting the significance of the -CHO group in aldehydes.

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Kritish Karki
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29 views9 pages

Untitled

Tollen's reagent is a mild oxidizing agent used to detect aldehydes, resulting in a color change due to the reduction of silver ions to metallic silver. The document outlines various tests for carbonyl compounds, including the sodium bisulphite test, Fehling's solution test, and Schiff's reagent test, each confirming the presence of aldehydes or ketones through observable reactions. Additionally, the document describes the preparation and observations for each test, highlighting the significance of the -CHO group in aldehydes.

Uploaded by

Kritish Karki
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© © All Rights Reserved
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TOLLEN’S REAGENT

Aldehydes are much more easily oxidized, than ketones, to carboxylic acids. Aldehydes
are oxidized not only by the same reagents that oxidize primary and secondary
alcohols, viz. permanganate and dichromate, but also by the very mild oxidizing agent
as silver ion. Oxidation by silver ion requires an alkaline medium under which conditions
it forms insoluble silver oxide, hence to dissolve this oxide a complexing agent
ammonia is added, which brings silver ion as diamminosilverI) ion, Ag(NH3)2• This
alkaline solution of silver nitrate in presence of ammonia is commonly known as Tollen's
reagent.

Note that in the above reactions, aldehydes lose the hydrogen that is attached to the
carbonyl carbon atom, and since ketones do not have such hydrogen, they are resistant
to oxidation.
Oxidation by Tollen's reagent is accompanied by colour change (due to reduction of Ag
ion to metallic silver), hence, the reagent is commonly used for detecting the presence
of an aldehyde in laboratory.

RCHO + Ag(NH3)2. → RCOO + Ag


Colourless solution. Silver mirror
Since, Tollen's reagent is a mild oxidizing agent, it does not attack carbon-carbon double
TOLLEN’S REAGENT TEST FOR
ALDEHYDE

Step 1: Take 1 milliliter of AgNO₃ solution in a sterile silver test tube.

Step 2: Gradually add a diluted NaOH solution to the test tube until a precipitate
forms.

Step 3: To dissolve the precipitate, add NH₄OH (ammonium hydroxide) until the
solution clears.

Step 4: Prepare Tollens’ reagent by adding approximately 0.5 mL (or 0.5 g) of the
speci ed substance to 2 mL of the prepared solution in a clean test tube.

Step 5: Warm the test tube gently in a water bath and observe the reaction.

OBSERVATION: Silver mirror on the inner wall of the test tube is formed

Inference: —CHO group con rmed

REACTIONS INVOLVED

AgNO₃ (aq) + NaOH (aq) → AgOH (s)} +NaNO₃ (aq)

AgOH (s)+ 2NH₄OH (aq) → [Ag(NH₃)₂]⁺ (aq) + H₂O (l) + OH⁻ (aq)

RCHO (aq)+ 2[Ag(NH₃)₂]⁺ (aq) + 3OH⁻ (aq)→ RCOO⁻ (aq) + 2Ag (s)+ 4NH₃ (aq)+ 2H₂O (l)
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ADDITION OF SODIUM BISULPHITE
Aldehydes, methyl ketones and cyclic ketones (not aromatic) react with sodium
bisulphite in presence of ethanol to give solid adduct.

NOTE
(i) A C-S bond is formed rather than C-O because S has more nucleophilic site than O.
(ii) Sulphite ion, SOz- is a large ion and hence reacts only if C —0 is not sterically
hindered; as in the case for RCHO,RCOCH3,&Cyclic Ketones.

The solid adduct is ltered from the ethanolic solution and then decomposed by acid or base
to regenerate the carbony! compound. Hence, this reaction is used for the puri cation and
separation of carbonyl compounds.
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S ODIUM BISULPHITE TEST

1. Take 1 milliliter of sodium bisul te (NaHSO₃) saturated


solution in a clean test tube.
2. Add a few drops of the speci ed substance (or its
ethanolic solution) to the sodium bisul te solution.

i) FOR ALDEHYDES

RCHO + NaHSO₃ → RCH(OH)SO₃Na

ii) FOR KETONES

RCOR + NaHSO₃ → R-C(OH)-SO₃Na-R

I I
—C = O. + NaHSO3 → — С — ОН
I
SO3Na
Sodium bisulphite addition compound

OBSERVATION : A crystalline precipitate is observed.

INFERENCE : Presence of carbonyl group


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F EHLING’S SOLUTION
Fehling's solution is prepared by combining two separate
solutions,known as Fehling's A and Fehling's B.
Fehling’s A is aqueous solution of copper(Il) sulphate,
which is deep blue.Fehling's B is a colorless solution of
aqueous potassium sodium tartarate(also known as Rochelle salt)
made in a strong alkali, commonly with sodium hydroxide.
Fehling solution is a deep blue solution of CuSO4.5H20,
sodium potassiumtartarate (Rochelle salt)
(Benedict's solution in which complexing agent is citarate ion
instead of tartarate ion) and NaOH in
F EHLING SOLUTION TEST

Step 1: Prepare Fehling’s solution by mixing equal volumes of Fehling’s


Solution A (aqueous copper(II) sulfate) and Fehling’s Solution B (alkaline
sodium potassium tartrate solution).

Step 2: Take a few milliliters of Fehling’s solution in a clean test tube.

Step 3: Add a few drops of the aldehyde (or the test substance) to the
Fehling’s solution.

Step 4: Gently warm the mixture in a water bath for a few minutes.

Step 5: Observe the result:

• If an aldehyde is present, the deep blue solution will turn into a reddish
precipitate of cuprous oxide (Cu₂O).

• If the substance is a ketone, there will be no reaction.

OBSERVATION : A reddish precipitate of Cu20 is obtained.

INFERENCE : Presence of —CHO group


2,4-Di nitrophenyl hydrazine test
Brady's reagent is an aqueous solution oF
2,4-dinitrophenyl hydrazine (DNP).It produces a
colored precipitate when it combines with carbonyl
chemicals, such as ketone and aldehyde. The melting
point of these precipitates is high. The carbonyl
compounds are con rmed by the precipitates' melting
points.A yellow or red crystalline ppt of aldehyde/
ketone 2,4-diphenoxylhydrazone is produced when
aldehydes and ketones react with 2,4-dinitro phenyl
hydrazine. It is a property of carbonyl compounds and
is employed to differentiate them from other organic
compound classes. This test is applied to carbonyl
compounds, such as ketones or aldehydes.
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S chi ’s Reagent

Schi ’s reagent is a chemical solution used as a qualitative test to detect the


presence of aldehyde functional groups in organic compounds. It is highly
sensitive and is often employed in both laboratory and diagnostic tests.

Step 1: Fill a clean test tube with approximately 1 mL of the test compound's
alcoholic or aqueous solution.

Step 2: Fill the test tube with 1 milliliter of Schiff's reagent.

Step 3: To guarantee adequate mixing, give the mixture a little shake.• Crucial:
Avoid heating the mixture since this may disrupt the process.

Step 4: Take note of the color shift:


• The solution will turn pink or magenta in the positive test (for aldehydes).
• Negative Test (for ketones): There won't be any discernible color shift.

Observation and Analysis:• Pink/Magenta Color: Verifies that an aldehydic group (-


CHO) is present.• No Color Change: Shows that aldehydes (such as ketones or
other chemicals) are not present.

The reaction must be carried out at room temperature because heat might upset
Schiff's reagent's sensitive equilibrium and provide false-negative findings, the
reaction must be conducted at room temperature.
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B ENEDICT’S SOLUTION TEST
The -CHO group in reducing sugars (e.g., glucose) reduces the blue
copper(II) ions (Cu²⁺) in Benedict’s solution to copper(I) oxide (Cu₂O), forming
a red precipitate.Aldehydes except benzaldehyde reduces Benedict solution

*Prepare the test tube: Take 1 mL of Benedict's solution in a


test tube.
* Add the organic compound: Add a few drops of the
organic solution to the test tube containing Benedict's
solution.
* Heat the mixture: Place the test tube in a water bath and
heat it.

OBSERVATION : Formation of reddish precipitate


Inference : —CHO Group con rmed
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