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What is Tollens Test ?

Tollens Test is a very useful method to distinguish between aldehydes and


ketones. This qualitative lab test is also referred to as the silver mirror test.

Tollens test is generally given by compounds having aldehydic group


(aldehydes,alpha-hydroxy ketones and formic acid-its -COOH behaves like
a aldehydic group). It gives a white ppt of Silver (where the silver salt is
reduced to silver metal and the aldehyde is oxidised to silver salt of
carboxylic acid.

Table of Contents :
 Tollens Reagent
 Alpha Hydroxy Ketone Tollens Test
 Tollens Reagent Preparation
 Tollens Test

Tollen’s Reagent :
Tollens Reagent refers to the chemical reagent which is used in the
detection of an aldehyde functional group, an aromatic aldehyde functional
group, or an alpha hydroxy ketone functional group in a given test
substance.

The Tollens Reagent is named after Bernhard Tollens, A German chemist


who discovered this reagent and its uses. Tollens reagent is a solution of
silver nitrate (AgNO3) and Ammonia (NH3).

Alpha Hydroxy Ketone Tollens Test :


Alpha hydroxy ketones are able to give a positive Tollens’ test since α-
hydroxy ketones have the ability to tautomerize to aldehydes, and the
aldehyde gives the Tollens’ test. An α-hydroxy ketone that cannot
tautomerize to a aldehyde won’t give a positive Tollens’ test, like benzoin.
Tollens Reagent Preparation :
Since Tollens Reagent has a relatively short shelf life, the reagent is not
commercially sold. Therefore, this reagent is often prepared directly in the
laboratory. One such method for the preparation of Tollens Reagent is
described below:

Step 1
A few drops of dilute NaOH are introduced to an aqueous solution of silver
nitrate. The aqueous solution of silver nitrate contain silver aquo complexes
wherein water acts as a ligand. The hydroxide ions now convert these
silver aquo complexes into silver oxides. This silver oxide (given by Ag 2O)
precipitates as a brown solid from this solution. The reaction can be written
as follows.

2AgNO3 + 2NaOH → Ag2O (brown ppt) + 2NaNO3 + H2O


Step 2
The brown precipitate of silver oxide generated in step 1 is now dissolved
with aqueous ammonia. The solution which formed from this addition of
aqueous ammonia contains the [Ag(NH3)2]+ complex. This complex is the
primary component of Tollens Reagent. The reaction can be written as:

Ag2O (brown ppt) + 4NH3 + 2NaNO3 + H2O → 2[Ag(NH3)2]NO3 + 2NaOH

Tollens Test :
When an aldehyde is introduced to the Tollens reagent, two things occur:

The aldehyde is oxidized by the Tollens reagent and forms a carboxylic


acid. This reaction can be written as follows:

The silver ions present in the Tollens reagent are reduced into metallic
silver. Generally, the Tollens Test is carried out in clean test tubes made of
glass. This is because the reduction of the silver ions into
metallic silver form a silver mirror on the test tube. This silver mirror is
illustrated in the example below.
Tollens test is commonly referred to as the Silver Mirror test due to the
formation of this layer of metallic silver on the test tube.

What is Fehling’s test?


One of the most popular tests used for the estimation or detection of
reducing sugars and non-reducing sugars is the Fehling’s test. The test
developed by German chemist H.C. Von Fehling is also used to
differentiate between ketone functional groups and water-soluble
carbohydrates.

Table of Contents :
 Fehling’s Solution
 Procedure
 Reactions of Fehling’s test
 Common Use of Fehling’s test

Fehling’s Solution :
Fehling’s test consists of a solution that is usually prepared fresh in
laboratories. Initially, the solution exists in the form of two separate
solutions which are labelled as Fehling’s A and Fehling’s B. Fehling’s A is a
solution containing copper(II) sulphate, which is blue. Fehling’s B is a clear
liquid consisting of potassium sodium tartrate (Rochelle salt) and a strong
alkali, usually sodium hydroxide. During the test solutions A and B are
prepared individually and stored.
The two solutions are later mixed in equal volumes to get the final Fehling
solution which is deep blue. The deep blue ingredient is the bis(tartrate)
complex of Cu2+. The tartrate tetra-anions serve as a chelating agent in the
solution.

Procedure:

The procedure can be conducted as follows;

 Add the sample in a dry test tube.


 Distilled water should be kept in another tube as control.
 Fehling’s solution is to be added in the tubes.
 The tubes must be kept in water bath.
 Make observations and record if there is any development of red
precipitate.

Notably, the result is positive if there is a formation of reddish brown


precipitate while the result is negative if there is no indication of such
change.

Precaution: Fehling’s solution is mostly corrosive in nature. Therefore, it is


always good to wear protective gear like goggles and gloves.
Reactions of Fehling’s Test :
In Fehling’s solution the reaction between copper(II) ions and aldehyde is
represented as;

RCHO + 2 Cu2+ + 5 OH− → RCOO− + Cu2O + 3 H2O

When tartrate is added:

RCHO + 2 Cu(C4H4O6)22− + 5 OH− → RCOO− + Cu2O + 4 C4H4O62− + 3 H2O

Common Uses of Fehling’s Test :


Some common uses of Fehling’s test are; it is used to determine whether a
carbonyl group is an aldehyde or a ketone. Aldehydes tend to get oxidized
and give positive result. Ketones apart from alpha-hydroxy-ketones do not
react.

Fehling’s test is also used as a general test for monosaccharides where a


positive result is obtained for aldose monosaccharides and ketose
monosaccharides. Apart from these, Fehling’s test is used in the medical
field to determine the presence of glucose in urine. It helps to know
whether the person is diabetic or not.

Iodoform test is used to check the presence of carbonyl compounds with


the structure R-CO-CH3 or alcohols with the structure R-CH(OH)-CH3 in a
given unknown substance.

The reaction of iodine, a base and a methyl ketone gives a yellow


precipitate along with an “antiseptic” smell. It also tests positive for a few
specific secondary alcohols that contain at least one methyl group in the
alpha position.
Iodoform Test Description :
When Iodine and sodium hydroxide are added to a compound that contains
either a methyl ketone or a secondary alcohol with a methyl group in the
alpha position, a pale yellow precipitate of iodoform or triiodomethane is
formed. It can be used to identify aldehydes or ketones. If an aldehyde
gives a positive iodoform test, then it must be acetaldehyde since it is the
only aldehyde with a CH3C=O group. Given below are a few example
reactions for positive iodoform tests.

Iodof
orm Test Description

Compounds That Give Positive Iodoform Test :


 Acetaldehyde
 Methyl Ketones
 Ethanol
 Secondary Alcohols that contain Methyl Groups in Alpha Position

Iodoform Test Mechanism :


First, the Hydroxide ion removes an acidic alpha hydrogen. This results in
the formation of an enolate ion. The enolate anion then goes on to displace
an iodide ion from the iodine molecule. This process repeats twice to give
R-CO-CI3. Now, a hydroxide ion forms a bond with the carbonyl carbon.
This leads to the reformation of the carbonyl group and the elimination of
the CI3– anion. An R-COOH group is also formed. The carboxylic acid group
and the basic CI3– ion neutralize each other. Thus the iodoform is
precipitated. The mechanism for this reaction is illustrated below:

Iodoform Test Mechanism

Thus, the pale yellow precipitate of iodoform is formed, which can be


identified by its characteristic “antiseptic” smell. The presence of the methyl
ketone is confirmed. The iodoform test is a very useful method to identify
the presence of these methyl ketones or acetaldehyde in an unknown
compound.
BIBLIOGRAPHY
To make this project,
I used my book and the internet
website…
www.wikepedia.com
https://byjus.com
I also taken help from my teacher
“MR. S.S PANDEY”

THANK YOU

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