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Solubility Test

Procedure for Water


Solubility
 Place 0.05 mL (approximately one drop) or
25 mg of the compound in a small test
tube, and add 0.75 mL of water in small
portions.
 Shake vigorously after the addition of each
portion of solvent, being careful to keep
the mixture at room temperature.
 If the compound dissolves completely,
record it as soluble.
Procedure for Testing with
Litmus Paper
 Dissolve 0.05 mL (approximately one drop) or
25 mg of the compound in 0.75 mL of water.
Using a stirring rod, place a drop of this
aqueous solution on both red and blue litmus
paper.
 If both litmus papers tum red, the compound
has a solubility class of SA
 If both litmus papers tum blue, the compound
has a solubility class of SB
 If both litmus papers remain their original color,
the compound has a solubility class of S1
Procedure for Ether
Solubility
 Place 0.05 mL (approximately one drop)
or 25 mg of the compound in a small
test tube, and add 0.75 mL of diethyl
ether in small portions.
 Shake vigorously after the addition of
each portion of solvent, being careful to
keep the mixture at room temperature.
 If the compound dissolves completely,
record it as soluble.
Procedure for Solubility in
Aqueous Acid or Base
 shake a mixture of 0.05 mL (approximately one
drop) or 25 mg of the unknown compound with 0.75
mL of 5% sodium hydroxide solution, 5% sodium
bicarbonate solution, or 5% hydrochloric acid
solution.
 Separate (filter if necessary) the aqueous solution
from any undissolved unknown, and neutralize it
with acid and base.
 Examine the solution very carefully for any sign of
separation of the original unknown.
 Even a cloudy appearance of the neutralized filtrate
is a positive test.
Procedure for Solubility in
Concentrated Acid

 Place0.6 mL of concentrated sulfuric acid


in a test tube, and add
0.05mL(approximately one drop) or 25 mg
of the unknown compound.
 For purposes of solubility classification,
unknowns that react with sulfuric acid to
produce heat and/or color changes should
be classified as soluble, even if the sample
does not appear to dissolve.
What Next?
PRELIMINARY
EXAMINATION
 Note whether the substance is
homogeneous, and record its
 physical state (solid or liquid),
 color,

 and odor.

 Ignition Test
Procedure for Ignition Test
 Place a 10-mg sample of the substance in a porcelain crucible lid (or any piece of
porcelain) and bring the sample to the edge of a flame to determine flammability.
 Heat the sample gently over a low flame, behind a safety shield. Heat the sample
until ignition has occurred.
 Note:
 (1) the flammability and nature of the flame (is the compound explosive?);
 (2) whether the compound is a solid, whether it melts, and the manner of its melting;
 (3) the odor of the gases or vapors evolved (caution!);
 (4) the residue left after ignition.
 Allow the lid to cool. Add a drop of distilled water. Test the solution with litmus paper.
Add a drop of 10% hydrochloric acid. Note whether a gas evolves. Perform a flame test,
with a platinum wire, on the hydrochloric acid solution to determine the metal present.

 an aromatic hydrocarbon (which has a relatively high carbon content) burns with
a yellow, sooty flame.
 Aliphatic hydrocarbons burn with flames that are yellow but much less sooty.
 As the oxygen content of the compound increases, the flame becomes more and
more clear (blue).
Summary and Applications
 The tests are extremely useful for decisions as to
whether further purification is necessary and as to
what type of purification procedures should be used.
 If various tests in this section indicate that the
compound is very impure, recrystallization or
chromatography is almost certainly required.
 Although liquids are very often easily analyzed by
gas chromatography, those that leave residues upon
ignition should not be injected into the gas
chromatograph
DETERMINATION OF
PHYSICAL PROPERTIES
 Melting Points, Boiling Points
and Freezing Points
 Specific Gravity  pycnometer
 Index of Refraction of Liquids 
refractometer
 OPTICAL ROTATION  polarimeter
B
C

Melting point (A), boiling point (B)


and freezing point (C) apparatus.
A
pycnometer
Refractometer
Polarimeter
QUALITATIVE ELEMENTAL
ANALYSIS
 Determine the existence of other elements,
such as nitrogen, sulfur, fluorine, chlorine,
bromine, and iodine.
 Knowledge of the elemental composition of
an organic compound being studied is
essential for the following reasons.
 Such knowledge aids in the selection of the
appropriate classification experiments, which
serve as tests for functional groups, and in the
selection of procedures for the preparation of
derivatives.
 Additionally, NMR spectra, IR spectra, and mass
spectra can be interpreted so that the structure of
the unknown is determined.
QUANTITATIVE ELEMENTAL
ANALYSIS
 Combustion and Related Analyses
Example
 11.55 mg of a compound produced
16.57 mg of carbon dioxide and 5.09
mg of water from combustion.
 Another 5.12 mg of the same
compound was found to contain 1.97
mg of chlorine.
 The molecular weight had been
previously determined to be 368.084
g/mole by another method.
11.55 mg of a compound
produced 16.57 mg of

carbon dioxide
The mg of C is determined by multiplying the weight of CO2
by the ratio of the atomic weight of carbon to the molecular
weight of carbon dioxide (C/C02).
 The percentage of C is then calculated by the ratio of mg of
C to the total weight of the sample
11.55 mg of a compound
produced 5.09 mg of water

from combustion
The mg of H is determined by multiplying the weight of H 0 2
by the ratio of the atomic weight of two hydrogens to the
molecular weight of water(2H/H20).
 The percentage of H is determined by the ratio of mg of H
to the total weight of the sample
5.12 mg of the same
compound was found to
contain

1.97 mg of chlorine
Since 1.97mg of Cl was found in 5.12mg of sample, then
the percentage of chlorine can be determined by the ratio
of mg of Cl to the weight of the sample used for the
analysis.
The percentage of oxygen is
determined by the difference
Each percentage is then
divided by the atomic weight
of that element to obtain the
ratio of the elements.
The ratios are then divided by
the lowest ratio (in this
example, 1.085).
 If a fraction is obtained that is not close to a whole
number, then all of the ratios are multiplied by whatever
integer is necessary to obtain whole-number ratios.
 the empirical formula is C6H9Cl2O2, with an empirical weight
of 184.042 g/mole.
 The formula weight, which had been previously determined
to be 368.084 g/mole, is then divided by the empirical
weight to obtain the number of empirical units, n.
 Then multiply the subscripts of the empirical formula by n
to obtain the molecular formula.
The unsaturation number
 From the molecular formula, the number of rings
and/or pi bonds can be determined.

 U = the unsaturation number


 C = the number of carbons
 X = the number of hydrogens plus halogens
 Y = the number of nitrogens plus phosphorus
 U can be interpreted as follows:
 U = 0: no double bonds, no triple bonds, no rings
 U = 1: one double bond or one ring
 U = 2: two double bonds or two rings or one
double bond and one ring or one triple bond
 U = 3: three double bonds or three rings or two
double bonds and one ring or two rings and one
double bond or one triple bond and one ring or
one triple bond and one double bond
 U = 4: usually a benzene ring
 U = 5: benzene plus one double bond or one ring
Example

 Calculate the unsaturation number


and give the interpretation for
C9H11NO!
Homework
 13.66 mg of a compound produced 10.71 mg of
carbon dioxide and 3.28 g of water. Another 4.86 g
of the same compound yielded 3.46 g of bromine.
The molecular weight is 673.72 g/mole.
 Calculate the percentages of carbon, hydrogen,
bromine, and oxygen in the sample.
 Determine
 the empirical formula
 the molecular formula
 the unsaturation number and its interpretation