Module 10 :Identification of Organic Compounds (Solubility Characteristics)

LABORATORY REPORT
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1. The following six substances have approximately the same boiling point and all are colorless
liquids. Suppose you were given six unlabelled bottles, each of which contained one of these
compounds. Devise an experimental procedure using simple chemical tests to identify the
contents of each bottle. (Each group may be assigned 2 substances)

Ethanoic acid Toluene

Propyl butanoate Diisobutylamine
Pentan-1-ol/ 1-Pentanol Styrene

2. A colorless liquid, C4H6O, having a boiling point of 97-98°C was found to be soluble in
water and also in ether. It gave a negative test for the presence of halogens, sulfur, and nitrogen.
It did however, give a positive test to 2,4-dinitrophenylhydrazine reagent. It gave a negative
result when treated with ceric nitrate solution and also Tollen’s reagent. Treatment with ozone
followed by hydrolysis in the presence of zinc gave formaldehyde as one of the products. What

is the structure and name of the colorless liquid?

 1.a. Ethanoic Acid
RCOOH (C1-C5)
Acid to litmus
ArSO3H
(Blue  Red)

1o, 2o, 3o Amines

Basic to litmus C1-C6
(Aliphatic) Ether soluble
(Red  Blue)

O
II
R-OH, RCHO, R-C-R C1-C5
Neutral to litmus R-COOR+, RCN, RCONH2

Polybasic acids, hydroxyacids, glycols, Ether-insoluble

Acid salts, amine hydrochlorides, amino acids
Strong RCOOH (>C6)
Soluble RSO3H, some phenols
Soluble
Ethanoic Water 5% NaHCO3
Acid

Insoluble
Weak RCOOH (>C5)
Insoluble
most phenols, enols, Sulfonamides
Soluble

5% NaOH 1o, 2o, 3o Amines (R>C8), ArNH2

ROH, RCHO
Miscellaneous - - - - - - - - - - - - - - - - - - - - cyclic ketones C6-8
neutral compounds Soluble RCOOR, RCOCH
containing N or S
(>C5), nitrites, Insoluble
amides, Soluble R-O-R (>C8)
mercaptans, sulfides

5% HCl 85% H3PO4

Insoluble Soluble Insoluble

Unsaturated hydrocarbons
Conc. H2SO4
R-O-R (>C8), some ketones,
aromatic compounds
Insoluble

Saturated hydrocarbons,
Haloalkanes, arylhalides,
some aromatic compounds
 1.b. Toluene

Acid to litmus
(Blue  Red) RCOOH (C1-C5)
ArSO3H

Basic to litmus
1o, 2o, 3o Amines
(Red  Blue) C1-C6
(Aliphatic) Ether soluble

O
Neutral to litmus II
R-OH, RCHO, R-C-R C1-C5
R-COOR+, RCN, RCONH2

Polybasic acids, hydroxyacids, glycols,

Acid salts, amine hydrochlorides, amino acids Ether-insoluble

Strong RCOOH (>C6)

Soluble RSO3H, some phenols
Soluble

Toluene Water 5% NaHCO3

Insoluble
Weak RCOOH (>C5)
Insoluble
most phenols, enols, Sulfonamides
Soluble

5% NaOH 1o, 2o, 3o Amines (R>C8), ArNH2

ROH, RCHO
Miscellaneous - - - - - - - - - - - - - - - - - - - - cyclic ketones C6-8
neutral compounds Soluble RCOOR, RCOCH
containing N or S
(>C5), nitrites, Insoluble
amides, Soluble R-O-R (>C8)
mercaptans, sulfides

5% HCl 85% H3PO4

Insoluble Soluble Insoluble

Unsaturated hydrocarbons
Conc. H2SO4
R-O-R (>C8), some ketones,
aromatic compounds
Insoluble

Saturated hydrocarbons,
Haloalkanes, arylhalides,
some aromatic compounds
 2. Methyl Vinyl Ketone

Acid to litmus RCOOH (C1-C5)

(Blue  Red) ArSO3H

(Red  Blue)
Basic to litmus 1o, 2o, 3o Amines
C1-C6
(Aliphatic)

O Ether soluble
II
Neutral to litmus R-OH, RCHO, R-C-R
R-COOR+, RCN, RCONH2
C1-C5

Polybasic acids, hydroxyacids, glycols,

Acid salts, amine hydrochlorides, amino acids
Ether-insoluble

Strong RCOOH (>C6)

Methyl Soluble RSO3H, some phenols
Vinyl Soluble
Ketone
Water 5% NaHCO3

Insoluble
Weak RCOOH (>C5)
Insoluble
most phenols, enols, Sulfonamides
Soluble

Miscellaneous 5% NaOH 1o, 2o, 3o Amines (R>C8), ArNH2

neutral compounds-------------------- ROH, RCHO
containing N or S cyclic ketones C6-8
(>C5), nitrites, Soluble RCOOR, RCOCH
amides,
mercaptans, sulfides Insoluble
Soluble R-O-R (>C8)

5% HCl 85% H3PO4

Soluble

Insoluble
Insoluble
Unsaturated hydrocarbons
Conc. H2SO4
R-O-R (>C8), some ketones,
aromatic compounds
Insoluble

Saturated hydrocarbons,
Haloalkanes, arylhalides,
some aromatic compounds
Conclusion:
The energy balance of intermolecular interactions between solute-solute, solvent-solvent, and
solute-solvent molecules controls solubility at the molecular level. The strength of intermolecular forces
varies, ranging from very weak induced dipole – induced dipole interactions to significantly greater dipole-
dipole interactions. The presence of electronegative atoms like N and O in polar functional groups like amines
(-NH2) and alcohols (-OH) also determines the polarity of organic compounds. Overall, polarity is a balance
of a molecule's non-polar and polar elements, and mentally breaking a molecule into its polar and non-polar
components can be helpful. In polar solvents, a bigger non-polar "organic" hydrocarbon component will make
the molecule less soluble, whereas more polar sections will make it more water soluble (polar solvent), and
vice versa for non-polar solvents. Additionally, the degree of branching in a compound's alkyl chain is another
element that can affect solubility. The intermolecular interactions between molecules are reduced when the
alkyl chain in a chemical is branched. This is frequently reflected in the branched molecule having a higher
water solubility than the straight-chain counterpart. This happens because branching compounds' molecules
are more easily separated from one another. However, there is a basic empirical rule that is quite useful and
practical. The simple rule is "like dissolves like," which is based on the polarity of the systems, with polar
molecules dissolving in polar solvents (water, alcohols) and non-polar molecules dissolving in non-polar
solvents (e.g. the hydrocarbon hexane).
Next, acetic acid has two carbons and is a simple monocarboxylic acid. Glacial acetic acid is a clear
colorless liquid with a strong vinegar flavor. When an acid dissolves in water, a proton (hydrogen ion) is
transferred to a water molecule, resulting in the formation of a hydroxonium ion and a negative ion, depending
on the acid. With ethanoic acid in solution in water, a hydrogen ion is transferred from the -COOH group to a
water molecule, forming an ethanoate ion and a hydroxonium ion, H3O+. This is a reversible reaction, and
in the case of ethanoic acid, only around 1% of the acid has reacted to create ions at any given moment.
Toluene, however, is an aromatic hydrocarbon composed of a benzene ring linked to one methyl group. It is
insoluble in water, with just carbon-carbon and carbon-hydrogen bonds, it is a highly non-polar molecule. It
can establish strong nonpolar van der Waals contacts with itself, but it cannot form significant attractive
interactions with the very polar solvent molecules.
Lastly, a colorless liquid, C4H6O, having a boiling point of 97-98°C was found to be soluble in water
and also in ether. Given that like dissolves like and the molecule is soluble in polar solvents, the substance
must include a polar group. The presence of heteroatoms nitrogen, sulfur, and halogen was not detected in
the compound, according to the statement. This suggests that the chemical has no heteroatoms N, S, or
halogens, according to our research. The presence of a carbonyl group in the unknown substance is indicated
by a positive test result with the 2, 4-dinitrophenylhydrazine reagent. When treated with ceric nitrate solution,
a negative result shows the absence of an allylic alcohol group. It was also tested negative on Tollen's
reagent, indicating that there is no aldehydic group present. According to our findings, formaldehyde is
generated as one of the results of ozone treatment followed by hydrolysis in the presence of Zn, indicating
the presence of unsaturation and terminal alkene. We can deduce that the unknown molecule is a ketone
named "Methyl Vinyl Ketone" or But-3-en-2-one in its IUPAC designation because it contains a carbonyl
group, formaldehyde as one of the products, and possesses unsaturated double bonds.