Chem 281 a

Organic Chemistry Laboratory

BSChE - II
_____________________ __________________
Name Course & Year

V2 – C1 10/10/2020
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Group no./Section Date

Activity No. 8
PROPERTIES OF ORGANIC COMPOUNDS WITH CARBONYL GROUP

Objective(s): To compare chemical reactivity of organic compounds with carbonyl

group.

Apparatus: test tubes, 10 ml graduated cylinder, Bunsen burner, water bath,

wire gauze, beaker(250 ml), test tube holder, test tube rack

III. Materials: Tollen’s reagent, formalin, benzaldehyde, formaldehyde, acetone,

Fehling’s A, Fehling’s B, Schiff’s reagent, 0.5% resorcinol, conc.
sulfuric acid, diluted sulfuric acid, ethanol, 10%sodium hydroxide, I2
in KI , potassium dichromate. formic acid, acetic acid, benzoic acid,
litmus paper, , acid, 3 g. soda lime, ethyl acetate, methyl salicylate,
amyl acetate, methyl benzoate
IV. Procedure:

Write your observations after each test, and summarize the results on the table provided.

A. Observe the following properties of the following

Properties formaldehyde benzaldehyde acetone formic acid acetic acid benzoic acid

Color colorless rusty-brown colorless colorless colorless colorless

strong-pickle
Odor almond-like pleasant pungent vinegar-like pleasant
like
not
Flammability flammable flammable flammable flammable flammable
flammable

Volatility high high high high high high

Solubility in
soluble insoluble soluble soluble soluble soluble
water

Solubility in
soluble soluble soluble soluble soluble soluble
alcohol

B. Tollen’s Test:

1. Place 3 to 5 drops of formalin, benzaldehyde, acetone, acetic acid, benzoic acid

solution, formic acid in six separate test tubes.
2. Add 3 to 5 drops of Tollen’s reagent to each test tube.
3. Mix the contents and warm gently in a water bath.

C. Fehling’s Test:

1. Place 3 to 5 drops of formalin, benzaldehyde, acetone, acetic acid, benzoic acid

solution, formic acid in six separate test tubes.
 2. Mix 3.0 ml of Fehlings A and 3.0 ml of Fehling’s B solution in a test tube.

3. Add 1.0 ml of Fehling’s solution prepared from 2 to each test tube in procedure 1.

D. Resorcinol Test:

1. Place 3 to 5 drops of formalin, benzaldehyde, acetone, acetic acid, benzoic acid

solution, formic acid in six separate test tubes.

2. Add 2 drops of 0.5% resorcinol solution to each test tube prepared in 1 then
shake the solution.

3. Incline the test tubes and add carefully 1.0 ml of concentrated sulfuric acid so
that the two layers do not mix.

Note the color at the junction of the two liquids.

E. Oxidation:

1. Mix in a test tube a pinch of potassium dichromate, 0.5 ml of concentrated

sulfuric acid and 0.5 ml of formaldehyde and 1 ml of water.
2. Heat gently and hold a piece of blue litmus paper in the vapor evolved.

3. Repeat the procedure using benzaldehyde instead of formaldehyde.

4. Repeat the procedure using acetone, formic acid, acetic acid and benzoic acid.
F. Iodoform Test:

1. To 1 ml of acetone add 1.5 ml of 10% NaOH solution and 0.5 ml of water.

2. Add drop by drop of solution of iodine in KI until prominent yellow color is

obtained. Warm gently.

3. Repeat the procedure using benzaldehye, formaldehyde, formic acid, acetic

acid & benzoic acid.
 Summary of Results:

Reagents/
Formaldehyde Benzaldehyde Acetone Formic acid Acetic acid Benzoic acid
Test

no silver less silver no silver no silver

Tollen’s silver mirror silver mirror
mirror mirror mirror mirror

layers of
layers of light
distinct layers cloudy
blue, light translucent
of clear light yellow clear blue
green and light blue blue green
green and and royal solution
rustic brown solution solution
Fehling’s royal blue blue
solution
solution solution Negative
Negative Negative
Result
Positive Result Result Result
Negative Result Negative
Result

distinct
distinct distinct distinct
layers of
layers of layers of layers of
distinct layers distinct layers clear
yellowish- clear clear
of reddish- of yellowish- yellowish-
brown and yellowish- yellowish-
white and clear brown and brown, rustic
clear light brown and brown and
red solution clear brown color and
Resorcinol solution
yellow
colorless
colorless colorless
solution solution solution
solution
Positive result Negative Result
Negative Negative Negative
Negative
result Result Result
result

blue to
Oxidation blue to red blue to red blue to red blue to red blue to red
red

Iodoform negative negative positive negative positive negative

V. Discussion of Results

Carbonyl group is a chemically organic functional group that is composed of a

carbon atom that is double-bonded to an oxygen atom. Carbonyl groups can be found in
several functional groups such as aldehydes, ketones, esters and many more. One distinct
feature of carbonyl group is its polarity. Carbonyl's polarity can do two things to the
property of a compound: (1) increases the melting and boiling point; (2) influences the
compound's solubility.

C=O
“Carbonyl group”
i.e., entity

X-C=O
“Carbonyl compounds”
i.e., members of the carbonyl group

Aldehyde is a common functional group in organic chemistry. It can be found in

perfumes or in natural and synthetic hormones. It is a carbonyl group that is single-
bonded to a hydrogen atom. A chemical formula of an aldehyde is RCHO where R
represents a hydrogen or carbon/hydrogen chain, CO represents the carbonyl and H
represents the hydrogen that is attached to the carbonyl chain. Aldehydes are considered
electrophiles because of its positive nature of the carbonyl carbon. Aldehydes' similarity
in the reactions is known to be that carbonyl is the site of reactivity in which the carbonyl
carbon of aldehyde is slightly positive because it is double bonded to an electronegative
oxygen. Formaldehyde and Benzaldehyde are some examples of Aldehydes.
Formaldehyde is a simple chemical compound that is made up of hydrogen, oxygen and
carbon. It has a chemical formula of CH2O. It is colorless, has a strong-pickle like odor,
flammable, high in volatility and soluble in both water and alcohol. Pure formaldehyde
which is in gas form is not advisable to use commercially because it tends to polymerize
exothermally and is possible to ignite. The Vapor from a formalin solution is flammable
and an explosion hazard when it is exposed to flame or heat. It has a number of uses for
pressed-wood products, glues, or in preserving anatomical specimens. On the other hand,
Benzaldehyde is an organic compound which consists of a benzene ring with a formyl
substituent. It is useful industrially and is the simplest aromatic aldehyde. It is has a
rusty-brown color with an almond-like odor. It is flammable and gives off yellow flame
with black gas which is known that the combustion is incomplete. It is insoluble in water
because the benzene ring is non-polar and water is polar. However, benzaldehyde is
soluble in alcohol.

Ketone is a compound that contains a carbonyl functional group that bridges two
groups of atoms. Its chemical formula is C12H24O while its general formula is RC(=O)R'
where R and R' are either alkyl or aryl groups. Acetone is an example of a ketone. It is a
colorless chemical that has a pleasant odor and is flammable. High in volatility and soluble
in both water and alcohol. Acetone molecules have polar carbonyl groups which allows
them to accept hydrogen bonds from other compounds. Acetone will completely dissolve
in water when added. Acetone also reacts with alcohol for it to form a hemiacetal. The
carbonyl group in the acetone is connected to the alkane propane which explains why
the IUPAC name for acetone is propanone. Acetone can be used in household products
such as cosmetics and personal care where it is much known for one of the main
components of a nail polish remover. It can also be used in manufacturing plastics and it
occurs naturally in the human body as a by-product of metabolism.

Carboxylic acids belongs to a class of organic compounds where a carbon atom is

bonded to an oxygen atom by a double bond and to a hydroxyl group by a single bond.
A fourth bond links the carbon atom to a hydrocarbon group. Carboxylic acids undergo
nucleophilic substitution reaction in which the nucleophile (-OH) is being substituted by
another nucleophile (Nu). The Carbonyl group gets polarized because the oxygen is more
electronegative than carbon and it pulls the electron density towards itself resulting for a
carbon atom to develop partial positive charge and the oxygen atom will develop a partial
negative charge. Formic, Acetic and Benzoic acid are examples of carboxylic acids. Formic
acid is the simplest of the carboxylic acids, it is a colorless, flammable chemical with a
pungent odor and has a high volatility. It forms hydrogen bonding with a water molecule
which concludes that it is soluble in water. It has a chemical formula of HCO2H and is
also called methanoic acid. It is not a typical carboxylic acid because it is distinguished
by its acid strength, failure to form an anhydride and also its reactivity as a reducing
agent. Acetic acid or Ethanoic acid is considered to be one of the most important
carboxylic acid. Colorless in color having a vinegar-like odor and it is flammable. Highly
volatile and soluble in both water and alcohol. Industrially, acetic acid is used in preparing
metal acetates that is used in some printing processes. Biologically speaking, acetic acid
is an important metabolic intermediate and it does occur naturally in body fluids and plant
juices. Another compound that belongs to the Carboxylic acids is Benzoic Acid. It is an
organic compound that consists of a carboxyl group attached to a benzene ring. With
that, it is said that benzoic acid is an aromatic carboxylic acid. It has a chemical formula
of C2H5COOH. It is a colorless compound with a pleasant odor; not flammable; has high
volatility and soluble in both water and alcohol. Although benzoic acid dissolves at a low
rate with cold water because most of its molecule is non-polar, its solubility increases if
the temperature of water increases. It is also soluble in alcohol because both alcohol and
benzoic acid are organic compounds.

Tollen's test or silver-mirror test is a qualitative laboratory test that is used to

distinguish between an aldehyde and a ketone. Aldehydes tends to readily oxidized which
gives off the presence of a silver mirror while ketones are not. The Tollen's reagent
oxidizes an aldehyde into the corresponding carboxylic acid. Aldehydes such as
Formaldehyde and Benzaldehyde depicts a silver mirror upon the addition of Tollen's
reagent however, no silver mirror was found in Ketones, having Acetone as an example
and the majority of the carboxylic acids which consisted of Acetic acid and Benzoic acid.
Only Formic acid gives off a slight silver mirror among all the three examples of Carboxylic
acids. Formic acid gives off a slight silver mirror because it acts as a strong reducing
agent because it is readily oxidised to form carbon dioxide and water. It reduces the Ag+
that is found in Tollen's Reagent as a silver diammine complex to give off element silver
which then deposits on the walls of the silvers that gives off that silver mirror.

Fehling's test is used in detecting or estimation of reducing sugars and non-

reducing sugars. It also differentiate between ketone functional group and water-soluble
carbohydrates. Fehling's solution is made up by two separate solutions that is labelled as
Fehling's A and Fehling's B. Fehling's A contains Copper (II) sulfate giving off a blue color
while the Fehling's B is a clear liquid that contains potassium sodium tartrate and a strong
alkali which is usually sodium hydroxide. Fehling's A and Fehling's B is then mixed giving
the solution a final color of deep blue. Positive results indicates the formation of reddish
brown precipitate while negative results indicates no change of color. Aldehydes are said
to give off a positive result however, only formaldehyde gives off a rustic brown solution.
Benzaldehyde, on the other hand has a negative result because the carbonyl group
happens to be an electron withdrawing group therefore the carbonyl group pulls the
electron from the electrion-rich benzene ring. The polarity of the C-H bond in the carbonyl
group is then reduced because the C-H bond now has a higher electron density and the
C-H bond becomes stronger. Fehling's solution cannot oxidize benzaldehyde because it is
a weaker oxidizing agent compared to Tollen's reagent. Acetone and Carboxylic acids
such as Acetone, Formic acid, Acetic acid and Benzoic acid gives off negative result.

Resorcinol is an organic compound and is one of the three isomeric benzenediols

which is white in color and soluble in water. Resorcinol reagent is used in Seliwanoff's
test. Seliwanoff's test is used to identify aldoses from ketoses. In order for a carbohydrate
to be an aldose, it needs and aldehyde group, same principle for ketose, it needs ketone
group. The formation of red color upon the reaction of the resorcinol to the compound
indicates a positive results. If no pink-red color, then the result is negative. Only
Formaldehyde gives off a positive reaction while Benzaldehyde, Acetone, Formic acid,
Acetic acid and Benzoic acid gives off negative results.
 For oxidation, all compounds have turned blue litmus paper to red. Therefore, all
of them are acidic. Although Acetone itself will not change the color of the litmus because
it is not an ionic substance which produces a change in pH but it has a tendency to turn
into an acid when water is added.

Iodoform test is used in checking if carbonyl compounds with the structure R-CO-
CH3 or alcohols having the structure R-CH(OH)-CH3 is present in a given unknown
substance. When Iodine and Sodium hydroxide are being added to a compound which
contains a methyl ketone or a secondary alcohol with a methyl group in the alpha position,
a pale yellow precipitate of iodoform or triiodomethane is formed. The presence of a pale
yellow precipitate indicates that the result is positive. Formaldehyde and Benzaldehyde
gives off a negative result upon adding NaOH, water and solution of iodine. The only
aldehyde that gives off a positive reaction to the iodoform test is Ethanal. Ketones like
Acetone gives off a positive result which is indicated by the presence of a pale yellow
precipitate while carboxylic acids gives off a negative result. Only Acetic acid from the
carboxylic acids group have given off a positive result given that acetic acid may form
acetic anhydride that reacts with iodoform reaction on refluxation.
VI. Significance of the Experiment

The significance of the experiment is to compare different compounds belong in

different groups with their reactivity in some reagents used. Tests were also conducted
specifically in detecting certain compounds present of to confirm if a given sample
contains a certain compound. Knowing the properties of these chemical compound can
be beneficial for later laboratory classes which requires a good foundation of Organic
Chemistry.
VII. References

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