CHEMISTRY 31.

1
ORGANIC CHEMISTRY
LABORATORY
EXERCISE 10:
Aldehydes and Ketones

Submitted by:
Abegail Mae S. Ramos
II-BS Biology
Laboratory Partners:
Gabriel Paulo G. Eleria
Marigold P. Araneta
II-BS Biology

ABSTRACT

2,4-DNPH is a positive test for both aldehydes and ketones. Test

compounds such as benzaldehyde, an aldehyde and methyl ethyl ketone
yielded yellow precipitate as an indication of positive test. However, these
compounds can be further analyzed as an individual entity and different from
each other. As for specific positive test for aldehdyes through Schiffs
reagent, benzaldehyde and formalin turned its color to magenta. Howver,
though methyl ethyl ketone was supposed to be colorless, giving a negative
result, it also turned into magenta. This happened because this test is
extremely sensitive and may give false positives. For specific test of methyl
ketones, iodoform test was conducted, yielding yellow precipitate to methyl
ethyl ketone and 2-butanol as well because it will also oxidize to methyl
ketone. Aldehydes can be classified further into aromatic and aliphatic.
Positive test in Benedicts test, yielding brick red precipitate would
distinguish aliphatic (formalin/formaldehyde) from aromatic. Errors occurred
in the experiment might be because of two factors, (1) not enough time for
the reaction to occur and (2) quality of chemicals obtained.

INTRODUCTION
Aldehydes and ketones are simple compounds which contain a
carbonyl group - a carbon-oxygen double bond. They are simple in the
sense that they don't have other reactive groups like -OH or -Cl attached
directly to the carbon atom in the carbonyl group - as you might find, for
example, in carboxylic acids containing -COOH. 2,4-dinitrophenylhydrazine is
often

abbreviated

to

2,4-DNP

or

2,4-DNPH.

solution

of

2,4-

dinitrophenylhydrazine in a mixture of methanol and sulphuric acid is known

as Brady's reagent. Details vary slightly depending on the nature of the
aldehyde or ketone, and the solvent that the 2,4-dinitrophenylhydrazine is
dissolved in. (Clark, Introducing Aldehydes and Ketones, 2003)
Any of a class of organic compounds, in which a carbon atom shares a
double bond with an oxygen atom, a single bond with a hydrogen atom, and
a single bond with another atom or group of atoms (designated R in general
chemical formulas and structure diagrams). The double bond between
carbon and oxygen is characteristic of all aldehydes and is known as the
carbonyl group. Many aldehydes have pleasant odours, and in principle, they
are derived from alcohols by dehydrogenation (removal of hydrogen), from
which process came the name aldehyde. (Aldehyde)
The aliphatic aldehydes are a homologous series of organic compounds
of carbon, hydrogen and oxygen, where the aldehyde functional group,
-C=O.H , is contained within the molecule. The general formula is
CnH2n+2.CHO. The aliphatic aldehydes are named by replacing "-e" at the
end of the alkane from which they are derived with "-al". Aromatic aldehydes
(e.g. benzaldehyde, C6H5.CHO), are also known which undergo a number of
chemical reaction which do nor occur for aliphatic aldehydes and which are
unique to aromatic aldehydes. (O'Leary, 2000)

A ketone is a compound containing a carbonyl group with two

hydrocarbon groups attached to it. Formal names for ketones include the
prefix from the alkyl group and the suffix -one. Two of the simplest are
propanone, marketed under the name acetone, and 2-butanone, marketed
under the name methyl ethyl ketone or MEK. (Shipman, Wilson, & Todd)
OBJECTIVES
The objective of the experiment was to be able to perform different
test to aldehydes and ketones test compounds in order to observe and
determine its positive and negative reactions.
METHODS
Methods were taken by following the procedures instructed from
Chemistry 31.1 Organic Chemistry on pages 73-75 with a slight modification
of using Methyl Ethyl Ketone instead of acetone as a test compound.

PRESENTATION OF RESULTS
Table 1. Formation of precipitate from test compounds added with 95%
ethanol and 2,4-dinitrophenylhyrdazine reagent.
Test compounds
Methyl Ethyl Ketone
Benzaldehyde
1-Butanol

Precipitate formed (in 15mins.)

+
+
-

Table 2. Benedicts Test

Test compounds

Color after heating

Methyl Ethyl Ketone

Benzaldehyde
1-Butanol

green
Blue green
No color change

Table 3. Schiffs Test

Color after
adding/before
heating
bluish
bluish
bluish

Test compounds
Formalin
Methyl Ethyl Ketone
Benzaldehyde

Color
Magenta
Pink
Pink (daker than Methyl Ethyl Ketone)

Table 4. Iodoform Test

Test compounds
Methyl Ethyl Ketone
Ethyl alcohol
2-Butanol

Color of precipitate formed

yellow
yellow
DISCUSSION

The 2,4-DNPH test is a positive test for aldehyde and ketone

compounds. The positive reaction of test compounds with are summarized
and generalized below.

The R and R in the reaction stands or any combination of hydrogen

and hydrocarbon group. For benzaldehyde, the reaction is shown below:

Figure 1. Reaction of benzaldehyde and 2,4-DNPH

For the two compounds, it is shown in the reaction, the boxed portion
the R and R groups has at least one attached hydrogen. This means that
benzaldehyde is an aldehyde. The reaction is known as a condensation
reaction. A condensation reaction is one in which two molecules join together
with the loss of a small molecule in the process. In this case, that small
molecule is water. (Clark, 2004). The mechanism is nucleophilic addition-

elimination reaction because first the 2,4-DNPH adds the benaldehyde in its
attached H to form water. Later, the formed water is then eliminated and the
product is an imine. For Methyl ethyl ketone, the structure is shown below:

Figure 2. Methyl Ethyl Ketone

As shown in the structure, it has an attached hydrocarbon group (as
boxed above). Therefore, in its reaction with 2,4-DNPH, since both has an
attached hydrocarbon group, the structure is a ketone. The same with
benaldehydes, the reaction is condensation reaction and the mechanism is
nucleophilic addition-elimination with formation of water and imine products.
Both benzaldehyde and Methyl Ethyl Ketone yielded with a yellow
precipitate because of the presence of carbon-oxygen double bond (Clark,
2004)
Benedicts solution is a specific positive test for presence of aliphatic
aldehyde that would yield brick red color. From the table 2 above, the results
of the tests were random and would not give a wise interpretation of the
reaction of aldehydes and ketones. The contributing factor of the errors
might be the quality of the chemicals given because of changes in color that
occurred to some test compounds, as well as the time it took for the reaction
to occur might be not enough on what was done in the experiment.
Nevertheless, the results must have been that only formaldehyde, also
known as methanal (Harrison, 1998) would react, yielding brick red
precipitate, being an aliphatic aldehyde. The reaction is shown below.

Figure 3. Benedicts positive reaction

Since benzaldehyde is an aromatic aldehyde, the expected result must
have been no reaction, retaining a blue solution. For Methyl Ethyl Ketone,

since it is a ketone and definitely not an aldehyde, it should have no

precipitate and would eventually retain its blue color of the solution.
Schiffs test is another positive test for aldehydes that would yield
colorless to magenta color. The reaction is shown below.

Figure 4. The positive reaction of Schiffs test

In figure 4, Schiffs reagent is made by adding the intensely colored
triphenylmethane dye called fuschsin to a solution of sodium bisulfate
(NaHSO3). The bisulfite reacts with the dye to produce a colorless solution.
This colorless solution will then react with aldehydes but not ketones to
produce a new triphenylmethane dye that also has a brilliant purple color.
(Experiment 13 Qualitative Tests for Carbonyls; Unknown Carbonyl).

In the experiments result from table 3, all test compounds had positive
result. However, Methyl ethyl ketone should have resulted into colorless color
since it is a ketone. The reason for this mishap might be because the
experiment was not handled accordingly because this test is extremely
sensitive and may give false positives. (Experiment 13 Qualitative Tests for
Carbonyls; Unknown Carbonyl).
The general reaction for Iodoform test is shown below.

Figure . Reaction of iodoform test

The iodoform reaction is a classical test for methyl ketones. A light

yellow precipitate of iodoform forms immediately with the methyl ketone 2pentanone. (Shriner, Fuson, Curtin, & Morrill, 2001).
Methyl Ethyl Ketone from the experiment had positive result, yielding
yellow precipitate. Secondary alcohols 2-butanol (isobutanol) will also oxidize
to methyl ketone and give a positive test with iodoform. (Experiment 6
(Organic Chemistry II) Identification of Ketones and Aldehydes)
CONCLUSION
Aldehydes and Ketones can be distinguished through several tests.
Even aldehydes can be further distinguished as aromatic or aliphatic through
a positive test in Benedicts of brick red which is characterized as aliphatic
aldehyde. In reaction with 2,4-DNPH, it is a positive test for both aldehydes
and ketones, forming a yellow precipitate imine. Certain tests have positive
specific reactions like in Schiffs reagent, it will only react with aldehydes,
forming colorless to magenta color, and iodoform test, specific test for
methyl ketones, forming yellow precipitate.

Q/A

1.) Differentiate the following pairs by giving the reagent used in the
exercise and the visible result:
a. Phenylactaldehyde and benzyl alcohol
Phenylactaldehyde is an aromatic aldehyde while
benzyl alcohol is an alcohol that will undergo oxidation in Iodoform
test.
Compounds

Phenylactaldehy
de
benzyl alcohol

Reaction
with 2,4DNPH
Yellow ppt.

Benedicts
Test

Schiffs
reagent

Iodoform
test

No rxn (blue)

magenta

No ppt.

N/A

N/A

N/A

Yellow ppt

b. 2-pentone and 3-pentone

2-pentone is a methyl ketone while 3-pentone is a diethyl
ketone.
Compounds
2-pentone
3-pentone

Reaction with
2,4-DNPH
Yellow ppt.
Yellow ppt.

Benedicts
Test
No ppt. (blue)
No ppt. (blue)

Schiffs
reagent
colorless
colorless

Iodoform test

Schiffs
reagent
colorless

Iodoform test

Yellow ppt.
N/A

c. Cyclohexanone and cyclohexyl methyl ether

Compounds

Reaction with
2,4-DNPH
Cyclohexanone
Yellow ppt.
cyclohexyl
Yellow ppt.
methyl ether

Benedicts
Test
No ppt. (blue)

d. 2-pentanone and 2-pentanol

2-pentanone is a methyl ketone while 2-pentanol is an
alcohol that will undergo oxidation in Iodoform test.
Compounds

Reaction with
2,4-DNPH

Benedicts
Test

Schiffs
reagent

Iodoform test

2-pentanone
2-pentanol

Yellow ppt.
n/a

No ppt. (blue)
n/a

colorless
n/a

Yellow ppt.
Yellow ppt.

2.) In the reaction of 2,4-dinitrophenylhydrazine with either aldehydes or

ketones you form imines which are derivatives of either aldehydes or
ketones, what is the purpose of these derivatives?
The reaction of aldehydes and ketones with ammonia or 1amines forms imine derivatives, also known as Schiff bases,
(compounds having a C=N function). This reaction plays an important
role in the synthesis of 2-amines. (Carbonyl Reactivity).
References
Aldehyde. (n.d.). Retrieved August 23, 2010, from Encyclopedia Britannica eb.com:
http://www.britannica.com/EBchecked/topic/13527/aldehyde
Carbonyl Reactivity. (n.d.). Retrieved August 23, 2010, from chemistry.msu.edu:
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm
Clark, J. (2004). Addition-Elimination Reactions of Aldehydes AND Ketones.
Retrieved August 23, 2010, from Chemguide.com:
http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html
Clark, J. (2003). Introducing Aldehydes and Ketones. Retrieved August 23, 2010,
from Chemguide:
http://www.chemguide.co.uk/organicprops/carbonyls/background.html
Experiment 13 Qualitative Tests for Carbonyls; Unknown Carbonyl. (n.d.). Retrieved
August 23, 2010, from Phoenix.liu.edu:
http://phoenix.liu.edu/~nmatsuna/che122/exp13.pdf
Experiment 6 (Organic Chemistry II) Identification of Ketones and Aldehydes. (n.d.).
Retrieved August 23, 2010, from SWC2.hccs.edu:
http://swc2.hccs.edu/pahlavan/2425L6.pdf
Harrison, K. (1998, July). Formaldehyde , Methanal . Retrieved August 23, 2010,
from Methanal @ 3Dchem.com: http://www.3dchem.com/moremolecules.asp?
ID=101&othername=Methanal
O'Leary, D. (2000). Aldehydes Aliphatic. Retrieved August 23, 2010, from
http://www.ucc.ie/academic/chem/dolchem/html/dict/aldehyde.html

Shipman, Wilson, & Todd. (n.d.). Ketones. Retrieved August 23, 2010, from
Hyperphysics***Chemistry: http://hyperphysics.phyastr.gsu.edu/hbase/organic/ketone.html
Shriner, R. L., Fuson, R. C., Curtin, D. Y., & Morrill, T. C. (2001). Iodoform Test for
Methyl Ketones. Retrieved August 23, 2010, from Chemistry Come Alive:
http://jchemed.chem.wisc.edu/JCESoft/CCA/CCA5/MAIN/1ORGANIC/ORG12/TRAM12/C
/0382204/MOVIE.HTM