Mapua Institute of Technology

School of Chemical Engineering and Chemistry

Chm143L

Organic Chemistry 2 Laboratory Report

Members: Student Number Program

Barangan, David Brian 2015100814 ChE

Dela Cruz, Napoleon Christian E. 2015102616 ChE

Diamante, April Joyce 2015108101 ChE

Dr. Dahlia Apodaca

Professor
 Experiment No.4

Aldehydes and Ketones

ABSTRACT:

Aldehydes and Ketones are organic compounds that contain a double bonded oxygen
bonded on a carbon, there many ways to classify these types of compounds first is the Benedict’s
Test in which aldehydes are converted to carboxylic acids with the use of copper, Tollens’ Test
uses silver ions to indicate a reaction has occurred. Another test used for identifying these
compounds is using sulfuric acid in alcohol and 2,4-dinitrophenylhydrazine in which ketone and
aldehydes would react. Sodium bisulfite test is also used to form a precipitate to indicate the
presence of a ketone group. And lastly Iodine in Sodium Hydroxide test is used to produce a
yellow precipitate in which this test is similar to the iodoform test when identifying alcohols.

INTRODUCTION:

Aldehydes and ketones are both carbonyl groups, were the difference is that aldehydes have a
hydrogen attached to the carbon with double bond to oxygen while ketones would have a methyl
or a carbon chain. Three types of reactions were tested in order to identify an unknown carbonyl
group if it is an aldehyde or a ketone. The first type of reaction is oxidation reaction, were two
types of test were conducted which are the Benedict’s test and Tollen’s test. The second type of
reaction is reactions with carbonyl group, were also two types of test were conducted which are
condensation reaction and addition reaction. The last type of reaction which only one test was
conducted is reaction of the alkyl group or haloform reaction. Aldehydes and ketones are also
important to society. Aldehydes and ketones are important to organic chemistry, although not a
lot of them are useful in creating commercial products, even so one compound of aldehyde is
mass produced everyday which is called formaldehyde, as it is founded in glue, shampoo,
deodorant, etc. For ketone, acetone is a well-known compound as it is founded at pharmaceutical
products, plastics, glue, and nail polish.
EXPERIMENTAL:

Methodology

Oxidation reaction, reactions of carbonyl group, and reaction of alkyl group (haloform
reaction) are what comprise this experiment. These tests aim to differentiate aldehydes and
ketones from one another. They differ in behavior at different reactions like oxidation. In order
to execute Benedict’s test, 1 mL of the test compound (acetaldehyde, benzaldehyde, and
acetophenone) shall be dissolved in 2 mL distilled water. Benedict’s reagent shall be added in an
amount of 2 mL. The mixture is then boiled. After boiling, the positive result will be indicated by
the change in color of the mixture. Tollen’s test is accomplished by adding 2 mL of test
compound (similar to the first test) to 1 mL of Tollen’s reagent. To induce the reaction, the
mixture shall be heated in a warm water bath. Excessive heating should be avoided because of
the mixture’s proneness to decomposition. Condensation, on the other hand, is completed by
adding 2-3 drops of acetaldehyde and 1 mL of 2,4-dinitrophenylhydrazine to 1 mL of 95%
ethanol. Allow the precipitate to form for some time. If no precipitate forms after 10 minutes,
dilute H2SO4 shall be added dropwise. This shall be repeated using acetone as the test compound.
1 mL of test compound (acetaldehyde and acetone) is added to 1 mL of NaHNO 3 solution.
Addition reaction will be observed if the mixture is to be shaken and left for 3-5 minutes.
Iodoform will be formed by adding 1 mL of test compound in 1 mL of water followed by 5 drops
of NaOH and iodine in potassium iodide solution (dropwise) until pale yellow mixture is
observed. Iodoform will form if the mixture is heated in a warm bath at 50 ˚C. Formation of
yellow precipitate (iodoform) indicates the presence of ketone.

RESULTS AND DISCUSSION

Aldehydes and ketones differ in their properties which are driven by their distinct
molecular structures. Although both of them encompass the carbonyl functional group,
aldehydes are known to exhibit an extra hydrogen atom in its structure contrary to ketones that
do not contain this extra atom. Because of this distinction, the two compounds behave differently
when reacted with various reagents. This difference in behavior is used to distinguish among
carbonyl compounds classifying them as either aldehydes or ketones
 This experiment used four tests in order to observe the chemical reactions that will take
place between the test compounds and several reagents. Benedict’s test utilizes Benedict’s
reagent which is composed of copper (II) ions. Aldehydes reduce the copper (II) ion producing
copper oxide which is a precipitate of color red or green. The test compound acetaldehyde
yielded green and red precipitate after the addition of Benedict’s reagent and heating the mixture
for a couple of minutes. A yellow separation was observed upon adding Benedict’s reagent to
benzaldehyde. No further change was observed after heating this mixture. These results verified
the idea that acetaldehyde is an aldehyde while acetone and acetophenone are ketones since both
compounds did not produce a red precipitate even after the addition of Benedict’s reagent. The
extra hydrogen atom in aldehydes allows reduction of copper to occur hence producing a
precipitate. Although benzaldehyde is an aldehyde, it did not produce a positive result in
Benedict’s test. This is because Benedict’s reagent cannot oxidize aromatic aldehydes. Tollen’s
test, on the other hand, produces a silver mirror upon its addition on an aldehyde. Only
acetaldehyde reflected this theory since it is the only compound that has extra hydrogen in its
parent chain. Benzaldehyde is deficient of free hydrogen in its parent ring reason why it yielded
a negative result in Tollen’s test. In actuality, Tollen’s reagent should be able to oxidize aromatic
aldehydes. Error might have been encountered while executing the experiment that hindered the
supposed reaction. Tollen’s reagent is inherent of the silver ion which is reduced to metallic
silver producing a silver mirror around the test tube if it were to be reacted with an aldehyde. The
observations are summarized in Table 1 below.

Table 1. Oxidation Reactions

Test Compounds Benedict’s Test Tollen’s Test

Green separation on top after
adding the reagent, green and Immiscible at first, silver mirror formed
Acetaldehyde
red precipitate resurfaced upon heating
upon heating
Brown mixture at first, grey mixture after
Acetone No change in mixture
heating
Pale yellow separation at
White precipitate in green mixture at first,
Benzaldehyde first, no change in mixture
brown separation after heating
upon heating
 Orange separation at first,
Brown mixture at first, brown separation
Acetophenone this separation remained after
was evident after heating
heating

2,4-dinitrophenylhydrazine test shows positive results for both aldehydes and ketones
producing a precipitate of colors ranging from yellow to orange. This test may be useful in
distinguishing compounds with a carbonyl group among other test compounds. Addition of
dilute H2SO4 to the mixture induced the production of precipitate in acetone confirming the
presence of carbonyl group in its structure. The addition of sodium bisulfite to the test
compounds acetaldehyde and acetone confirms the presence of carbonyl group. This test is used
best on aldehydes since it may produce crystals purifying the impure aldehyde. A positive test is
obtained for ketones that have a methyl group attached to one of the hydrocarbons since bulky
groups hinder the occurrence of reaction (“Simple Addition of Aldehydes and Ketones”). The
observations are summarized in Table 2 below.

Table 2. Reactions of the Carbonyl Group

Test Compounds 2,4-dinitrophenylhydrazine Sat’d NaHSO3

No precipitate was formed
Acetaldehyde Immiscible at first forming an emulsion
until H2SO4 was added
Acetone Precipitate formed upon
White separation
addition of reagent

Iodoform test may also be applied in the identification of methyl ketones wherein
appearance of yellow precipitate is indicative of a positive test. Although acetaldehyde is not a
methyl ketone, this aldehyde compound remained to exhibit a positive iodoform test due to the
methyl group which may be removed and produce iodoform (CHI 3); it is the only aldehyde that
produces a positive test when reacted with 8M of NaOH. The observations are summarized in
Table 3 below.
Table 3. Reactions of th Alkyl Group

OO
Test Compounds
Yellow mixture started to form, the color became stronger when
Acetaldehyde
placed in a warm water bath
Clear mixture was obtained at first, pale yellow color was observed
Acetone after adding 6 drops of iodine from potassium iodide solution, the
color became more evident upon heating

CONCLUSION

The extra hydrogen atom in the structure of aldehyde allows it to be oxidized more
effectively than ketones. This is the reason behind the different behavior of these two compounds
when reacted with various reagents. The experiment accentuates on the chemical basis behind
classification of aldehydes and ketones utilizing several tests in order to establish difference
between the provided test compounds. Benedict’s reagent and Tollen’s reagent are used to
distinguish aldehydes from ketones since these two tests yield positive results when reacted with
an aldehyde. Acetaldehyde exhibited positive results in the two tests while benzaldehyde
remained to show negative results even though it is an aldehyde. Its behavior in Benedict’s
reagent is expected since this reagent is not capable of reducing aromatic aldehydes. Both 2,4-
dinitrophenylhydrazine and saturated sodium bisulfite distinguish which of the test compounds
have carbonyl groups in their structures. The positive result in this test is implied by precipitation
(yellow mixture) or crystallization. The crystallization result of sodium bisulfite reaction with
aldehydes makes it useful method in purifying aldehydes. Iodoform method is not only used in
alcohols and ketones, it may also be used in determining whether a certain compound contains an
alkyl group in its structure. Although iodoform test is usually advisable for methyl ketones,
acetaldehyde remained to yield a positive result since its structure is quite similar to ketones
wherein the methyl group outside the structure may be substituted with iodoform (CHI 3).
Completion of reaction in iodoform test is indicated by the resurfacing of yellow precipitate in
the mixture. Having tried all these tests and having been able to validate the theories allowed the
students to thoroughly grasp the difference between ketones and aldehydes.

REFERENCES
Aldehyde, Ketone, Carboxylic Acid. (n.d.). Retrieved February 17, 2017, from
http://www.livewebtutors.com/homework-help/chemistry/properties-and-uses-of-
aldehydes-ketones-carboxylic-acid

Carbonyl Reactivity. (n.d.). Retrieved February 17, 2017, from

https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/aldket1.htm