Discussion：

Chromic acid test can be used to differentiate aldehyde and ketone. Since chromic
acid is a strong oxidizing agent. It can oxidize alcohols and aldehydes to form carboxylic acid
but it will not oxidize ketone. The change in colour from orange solution to green solution
shows a positive test which due to the change in oxidation state of the chromic metal. The
chromic acid will be reduced from Cr6+ (orange) to Cr3+(green) which undergoes reduction.
Tollen’s reagent is a test used to identify a carbonyl compound whether the compound is
aldehyde or ketone. Aldehyde is readily oxidized to form carbocylic acid but ketone is not.
The positive result in Tollen’s reagent is the formation of silver mirror or black precipitate in
the solution. For Fehling’s test, the functional group of aldehyde can be tested via reduction
of deep blue solution of copper(II) to a formation of brick red precipitate. In DNP test,
Brady’s reagent is usually used to test on aldehydes and ketones. The formation of yellow,
orange or red precipitate give the positive result to the compounds with carbonyl groups.
Besides, iodoform test is functioned as the test for α-methyl group present in aldehydes,
ketones and secondary alcohols. The positive result can be seen through the formation of
yellow precipitate in the particular test.

For unknown A, it gave negative results in the chromic acid test and Tollen’s test. The
unknown A cannot be oxidized by the chromic acid and Tollen’s reagent. In Fehling’s
solution, there is a formation of greenish brown precipitate in this test. The unknown A in this
test gave negative result because unknown A cannot shows positive test in the first two tests
respectively. So, it is believed that the formation of the precipitate is due to the reaction
between the unknown A and the metal in Fehling’s reagent. Unknown A shown a positive
result in DNP test which the reddish orange precipitate was formed. This is because the C=O
functional group is exists in the unknown A. In iodoform test, the present of yellow
precipitate indicated that the positive test for iodoform test. This is shows that unknown A
consists of α-methyl group in its structure. The unknown A is predicted has ketone group,
with more specified is predicted as acetophenone.

In chromic acid test, unknown B gave a positive result which orange solution is
turned to green solution. This is shows that unknown B is oxidized by the chromic acid. So,
the following test Tollen’s test and Fehling’s test also shows the positive results. The
formation of silver mirror and brick red precipitate are formed in the Tollen’s test and
Fehling’s test respectively. In DNP test, unknown B also gave the positive result which the
bright yellow precipitate is formed. This is indicates that the unknown B has the functional
group of C=O in its compound. However, the unknown B did not give a positive result in the
iodoform test. So, we can predict that the α-methyl group is absent in the compound.
Unknown B is predicted as benzaldehyde which is categorized into aldehyde group.
 The positive result in chromic acid test for unknown C shows that the reduction of
Cr6+ to Cr3+ take places in the reaction. Unknown C is considered as undergoes oxidation
via chromic acid test since chromic acid is a strong oxidizing agent. The unknown C cannot
be oxidized by Tollen’s reagent and Fehling’s solution. Unknown C gave negative result in
both tests which no formation of silver mirror in Tollen’s test and no brick red precipitate in
Fehling’s solution. It is also show a negative result in DNP test due to no precipitate form.
This is shows that unknown C does not consist of α-methyl group in its compound. Unknown
C is predicted as isopropyl alchol which is under the category of alcohol.

There are four tests to differentiate phenolic compound which include solubility,
acidity, bromine water test, and ferric chloride test. Solubility is used to differentiate the
compound is completely soluble, partially soluble or non soluble in water. Solubility of
compounds is the tendency of the compound to form the hydrogen bonding with the water
molecules. The formation of homogeneous solution after the compound dissolved completely
in water indicates the positive result. In the acidity of phenolic compound test, the strong base
will tend to react with the compound by deprotonating the phenolic compound. Normally,
sodium hydroxide and sodium carbonate are strong enough bases to dissolve most water
insoluble phenols instead of sodium bicarbonate. The degree of dissociation can be shown in
the solubility of the phenolic compound in the strong base solution. Positive result is
indicated by the tendency of phenolic compound dissolve in all the base solution. In bromine
water test, the decolouration of yellow solution shows a positive test which is followed by the
formation of white precipitate. In ferric chloride test, phenol tends to react with ferric
chloride to give a coloured complex. The change of colour in the solution shows the positive
result.

Unknown D is soluble in the water and tends to form a homogeneous solution.

Similarly, it is also dissolved completely in sodium hydroxide, sodium carbonate, and sodium
bicarbonate. The acidity of unknown D can be shown in the solubility in sodium hydroxide,
sodium carbonate, and sodium bicarbonate. Unknown D is soluble in all base solution
although it is a weak acid. However, it is a water soluble phenol. So, it can soluble in the
three base solutions. In the bromine water test, the unknown D had decolourized the yellow
bromine water. This is shows that unknown D is undergoes bromination to form a brominated
phenolic compound. In the ferric chloride test, the solution turns to purple solution after ferric
chloride was added. This is shows that unknown D is not an ordinary alcohol. Thus, unknown
D is predicted as phenol.

For unknown E, it is soluble in water and form homogenous solution. However,

unknown E is only soluble in sodium hydroxide but not in sodium carbonate and sodium
bicarbonate either. This is shows that unknown E is a water-insoluble phenol and is
categorized as a weak acid. In bromine water test and ferric chloride test, the colours of
bromine water and ferric chloride were remained unchanged in each test. So, this is means
that unknown E does not react with bromine and ferric chloride. As a result, the unknown E
is considered as ordinary alcohol.