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 Schiff’s 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 Benedict’s 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. A 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. [ CITATION Jim031 \l 1033 ]

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.
[ CITATION Ald10 \l 1033 ]

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. [ CITATION Don00 \l 1033 ]

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. [ CITATION Shi10 \l 1033 ]
 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 Precipitate formed (in 15mins.)

Methyl Ethyl Ketone +
Benzaldehyde +
1-Butanol -

Table 2. Benedict’s Test

Test compounds Color after heating Color after

adding/before heating
Methyl Ethyl Ketone green bluish
Benzaldehyde Blue green bluish
1-Butanol No color change bluish

Table 3. Schiff’s Test

Test compounds Color

Formalin Magenta
Methyl Ethyl Ketone Pink
Benzaldehyde Pink (daker than Methyl Ethyl Ketone)

Table 4. Iodoform Test

Test compounds Color of precipitate formed

 Methyl Ethyl Ketone yellow
Ethyl alcohol -
2-Butanol 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. [ CITATION Jim04 \l 1033 ] . 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 benaldehyde’s, 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 [ CITATION Jim04 \l 1033 ]

Benedict’s 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 [ CITATION Kar98 \l 1033 ] would react, yielding brick red precipitate, being an aliphatic
aldehyde. The reaction is shown below.

Figure 3. Benedict’s 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.

Schiff’s 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 Schiff’s test

In figure 4, Schiff’s 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.
[ CITATION Exp10 \l 1033 ].

In the experiment’s 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. [ CITATION Exp10 \l 1033 ].

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 2-pentanone. [ CITATION Shr01 \l 1033 ].

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. [ CITATION Exp101 \l 1033 ]

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 Benedict’s 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 Schiff’s 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 Reaction with Benedict’s Schiff’s Iodoform test

 2,4-DNPH Test reagent
Phenylactaldehyd Yellow ppt. No rxn (blue) magenta No ppt.
e
benzyl alcohol 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 Reaction with Benedict’s Test Schiff’s Iodoform test

2,4-DNPH reagent
2-pentone Yellow ppt. No ppt. (blue) colorless Yellow ppt.
3-pentone Yellow ppt. No ppt. (blue) colorless N/A

c. Cyclohexanone and cyclohexyl methyl ether

Compounds Reaction with Benedict’s Test Schiff’s Iodoform test

2,4-DNPH reagent
Cyclohexanone Yellow ppt. No ppt. (blue) colorless
cyclohexyl Yellow ppt.
methyl ether

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 Benedict’s Test Schiff’s Iodoform test

2,4-DNPH reagent
2-pentanone Yellow ppt. No ppt. (blue) colorless Yellow ppt.
2-pentanol n/a n/a n/a 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 1º-amines forms imine
derivatives, also known as Schiff bases, (compounds having a C=N function). This
reaction plays an important role in the synthesis of 2º-amines. [ CITATION Car10 \l 1033 ].
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