15- ALDEHYDES, KETONES AND SACCHARIDES

Name: Del Rosario, Bianca Elaine G.

Year and Section: DMD-1A
 
QUESTIONS:

Identify the type of reaction involved in the following:

 
a. ) 2,4-dinitrophenylhydrazine test

Aldehydes and ketones react with 2,4-dinitrophenylhydrazine gives a yellow to

orange precipitate.
The chemical reaction is given below.

A positive result is a red-orange precipitate of 2,4-dinitrophenylhydrazone

 
b. ) Sodium bisulfite test

Aldehydes and ketones combine with sodium bisulfite to for well crystallized water
soluble products known as “aldehyde bisulfite” and “ketone bisulfite”.
The chemical reaction is given below.

A positive result is a water-soluble crystalline bisulfite addition product

 
c.) Tollen’s test

This test is also called silver mirror test. Tollens reagent consists of silver ammonia
complex in ammonia solution. Aldehydes reacts with Tollens reagent gives a grey
black precipitate or a silver mirror. Always a freshly prepared Tollen’s reagent should
be used. Aldehydes are oxidised to the corresponding acid and silver in Tollens
reagent is reduced from +1 oxidation state to its elemental form. Generally ketones do
not respond to this test.
RCHO + 2[Ag(NH3)2]OH → R-COONH4 + 3NH3 + H2O + 2Ag↓(silver mirror)
Apart from aldehydes some other compounds also respond to Tollen’s test, but the
presence of aldehydes is conformed when the given substance shows positive test for
Tollens test but if the given compound passes 2,4-dinitrophenylhydrazine test.
A positive result is a silver mirror adhering to the walls of the container [this is due
to the reduction of silver nitrate to metallic silver] 

d.) Fehling’s test

Feling’s solution is a complex compound of Cu2+. When aldehyde compound is

treated with fehling’s solution Cu2+ is reduced to Cu+ and the aldehyde is reduced to
acids. During the reaction a red precipitate is formed.

Aromatic aldehydes do not respond to fehling’s test. An aqueous solution of the

compound may be used instead of an alcoholic solution. Formic acid also give this
test.
A positive result is change of color from dark blue to olive green and finally to brick
red precipitate [this is due to the reduction of cupric to cuprousions]

 
2. Why does glucose give a positive Fehling’s test?

It will give a positive result for aldose monosaccharides (due to the oxidisable

aldehyde group) but also for ketose monosaccharides, as they are converted to aldoses
by the base in the reagent, and then give a positive result. Fehling's can be used to
screen for glucose in urine, thus detecting diabetes.
 
 
3. What is the clinical significance of the sodium nitroprusside test?
 Sodium nitroprusside is used to detect illicit substances, such as secondary amines, in
forensic laboratories (Simon's test). It is used to control blood pressure and to treat
hypertension.
 
 
4. What is the basis of the Molisch test being used to differentiate aldehydes and
ketones from carbohydrates?

 The Molisch test uses a color change system to show the presence of aldehydes when
interacting with a phenol. A carbohydrate that has been dehydrated will form an
aldehyde and thus react with the phenol to form a purple color change. A ketone will
not react this way because they do not have a single hydrogen attached to the C=O
bond, it has a full hydrocarbon group, making it less likely to oxidize.

 
 
5. What is specific rotation?
 
Specific rotation of a compound is a characteristic property of the compound as long
as the temperature, the wave length of the light, and, if a solution is used for the
experiment, the solvent are specified. The units of specific rotation are degreesmLg-
1dm-1. However, since the units of specific rotation are always the above,
traditionally, specific rotation is reported without units.
 
 
6. What property of D-Glucose is responsible for the observed specific rotation?
 Compounds which rotate the plane of polarization of a beam of plane polarized light
clockwise are said to be dextrorotary, and correspond with positive specific rotation
values.
 
 
7. What is the importance of the phenylhydrazine test?

The osazone test will give some indication whether a sugar is either glucose or

lactose, but the solubility of the crystals formed should be determined to verify the
microscopical appearance, as so many factors influence the crystalline structure

Ex:for sucrose one gets a mixture of glucosazone and fructosazone on the basis of
components of sucrose.