CHEMISTRY LABORATORY 203, SEC A

Activity No. 10

Title: Aldehydes and Ketones

Rating
Name: Pangan, Judith Ann E. Group No. 4 1 Objective ___
2 Data, Results and
Date Performed: January 31, 2017
Discussion ___
Date Submitted: February 14, 2017 3 Q& A ___
4 Conclusion ___
5 N&F -
___
Total Score ___

I Introduction:

Aldehydes and Ketones represent an important class of organic molecules containing a

carbonyl carbon. The common names of ketones are derived by naming two alkyl

or aryl groups bonded to the carbonyl group.

II Objectives: to be able to

A. Distinguish aldehydes from ketones through Schiffs test, tollens test and fehlings
test.
B. Determine the chemical and physical properties of aldehydes and ketones through the
presence of the carbonyl group.

III. Data, Results & Discussion:

A. Test for Carbonyl Group

1. 2,4 DNPH

Name of Compounds Reagents Results Explanation

Acetophenone 2, 4 dinitro- Yellow precipitate Formation of a

Benzaldehyde phenylhydrazine Orange precipitate precipitate therefore
Salicylaldehyde Yellow precipitate indicates the presence
of an aldehyde or
 ketone. The
precipitate from this
test also serves as a
solid derivative.

RESULTS & DISCUSSIONS:

The nucleophilicity of 2,4 dinitrophenylhydrazine, attacks the electrophilc aldehyde and ketone
compounds by bonding the terminal nitrogen in the amino group to the carbon-oxygen double
bond forming an intermediate compound.

Aldehydes and ketones react with 2,4-dinitrophenylhydrazine reagent to form yellow, orange, or
reddish-orange precipitates, whereas alcohols do not react.

2. Sodium Bisulfite Test

Name of Compounds Reagents Results Explanation
Benzaldehyde 40% NaHSO3 in
Acetone ethanol

B. Test for Aldehydes

1 Schiffs Test

Name of Compounds Reagents Results Explanation

Formalin Schiffs reagent Aldehydes react
Acetophenone with Schiff's
Acetone reagent to produce
Benzaldehyde a color change
(magenta-colored
addition product).
Schiff reagent acts
as a nucleophile
that adds to the
carbonyl group of
an aldehyde

RESULTS & DISCUSSIONS:

The sulfur in the bisulfite ion acts as a nucleophile and adds to the carbonyl carbon.
Because this is such a bulky nucleophile, it will add only to a relatively sterically
unhindered carbonyl. This requires that the carbonyl be part of an aldehyde in
which one of the R groups is the very small hydrogen, or a ketone having small R
and Rgroups. A ketone having large groups attached to the carbonyl will not react
with bisulfite. Nucleophile is extremely bulky, a ketone, which is more sterically
crowded than an aldehyde at the carbonyl carbon, does not react with Schiff's
reagent, and thus does not produce the magenta color. Production of the magenta
color therefore indicates that the unknown is an aldehyde 3 and not a ketone

2 Tollens Test
Name of Compounds Reagents Results Explanation
Formalin Tollens reagent
Benzaldehyde
Glucose
Acetone

Ketones are not oxidized by Tollens reagent, so the treatment of a ketone with Tollens reagent
in a glass test tube does not result in a silver mirror (Figure 1; right).

3 Fehlings Test
Name of Compounds Reagents Results Explanation
Formalin Fehlings A
Glucose Fehlings B
Benzaldehyde
Acetone

C. Test for Methyl Ketone

1. Sodium Nitroprusside Test
Name of Compounds Reagents Results Explanation
Acetone 5% sodium
Ethyl Methyl Ketone nitroprusside
Glacial Acetic Acid
3% NaOH

2. Iodoform Test

Name of Compounds Reagents Results Explanation

Acetone Iodine in Kl
Ethyl Methyl Ketone solution
Ethyl Acetate 10% NaOH

The iodoform test indicates the presence of an aldehyde or ketone in which one of
the groups directly attached to the carbonyl carbon is a methyl group. Such a
ketone is called a methyl ketone. In the iodoform test, the unknown is allowed to
react with a mixture of iodine and base. Hydrogens alpha to a carbonyl group are
acidic and will react with base to form the anion, which then reacts with iodine to
form an alpha-iodo ketone. In a methyl ketone, all three alpha hydrogens are
substituted by iodine in this way to form the triiodo compound, which then reacts
with more base to form the carboxylic acid salt plus iodoform, a yellow precipitate.
Formation of a yellow precipitate therefore indicates the presence of a methyl group
directly attached to the carbonyl.

The mechanism of the iodoform reaction is that of alpha-halogenation of a carbonyl

compound under basic conditions, followed by nucleophilic displacement of the
resulting triiodomethyl group by hydroxide

D. Test for Benzaldehyde

Name of Compounds Reagents Results Explanation

Test for Benzaldehyde Benzaldehyde

E. Mollischs Test

Name of Compound Reagents Results Explanation

Glucose Molischs Reagent
Starch
Benzaldehyde Conc. H2SO4
 III. Answer the questions:
a. Explain the reactivity of aldehydes and ketones towards nucleophilic reagents.
b. Give the principle involved in the following
c. Why does glucose give a positive Fehlings test?
d. What is the clinical significance of sodium nitroprusside test?
e. What other compounds gives positive iodoform test? Explain.
f. What is the significance of Molisch test?
g. What is the basis of Molisch test?
IV.

V. Conclusion:

In this experiment,

Why glucose gave a positive result in fehling's test

-Glucose contains aldehyde group, so it gives positive fehling's test.

-Sodium nitroprusside test is used to determine glucose level in blood in diabetic patients.
-Molisch test is positive only for carbohydrates and not for aldehydes and ketones This test is useful for
identifying any compound which can be dehydrated to furfural or hydroxymethylfurfural in the presence of
H2SO4. Furfural is derived from the dehydration of pentoses and pentosans, while hydroxymethylfurfural
is produced from hexoses and hexosans. But open chain aldehydes and ketones dont give this test
-The specific rotation of a chemical compound [] is defined as the observed angle of optical rotation
when plane-polarized light is passed through a sample with a path length of 1 decimeter and a sample
concentration of 1 gram per 1 millilitre
-muta rotation is responsible for the observed specific rotation.

clinical significance of the Sodium Nitroprusside Test?

Sodium nitroprusside detects cysteine in the urine (cystinuria). The -SH group reacts with Na3Fe(CN)5NO
to give a red color.

"A qualitative test for cystinuria; following the addition of sodium cyanide to the urine, the further addition
of nitroprusside produces a red-purple colour if the cyanide has reduced any cystine present to cysteine."

Significance of molisch test

Sensitive chemical test for the presence of carbohydrates based on the dehydrations of carbohydrates by
sulfuric acid to produce an aldehyde which condenses with 2 molecules of a- naphthol though other
phenols (resorcinol, thymol) also give colored products resulting in a purple colored compound indicated
by the appearance of a purple rings at the interface between the acid and test layers.
The test solution is combined with a small amount of Molisch's reagent (-naphthol dissolved in ethanol)
in a test tube. After mixing, a small amount of concentrated sulfuric acid is slowly added down the sides of
the sloping test-tube, without mixing. A positive reaction is indicated by a purple ring forming at the
interface between the acid and test layers.

All carbohydrates -- monosaccharides, disaccharides, and polysaccharides -- should give a positive

reaction. Glycoproteins also give a positive reaction. Pentoses are dehydrated to furfural; hexoses are
dehydrated to hydroxymethylfurfural. Either of these aldehydes, if present, will condense with two
molecules of naphthol to form a purple-colored product. >O2 (furfural) + Reactions:

1. C5H10O5 (pentose) + (conc.) H2SO4 C5H4O2 + 3 H2O

2. C5H4 + 2 C10H8OH (-naphthol) colored product

Basis for molisch

The test is based on the dehydration of the carbohydrate by sulfuric acid to produce an aldehydes. The
formation of purple ring indicates that it is a positive reaction to carbohydrates. On the other hand,
Ketones will not react with molisch 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.