GROUP 1 – SOLUBILITY and or color changes classified as

soluble.
Solubility – In liquid, it is controlled by the
energy balance of Intermolecular Forces Solubility of Organic Compounds
between solute-solute and solute-solvent
1. Water Solubility – depends on the
molecules.
number of carbons, size of the chain
“Like dissolves Like” and presence of polar part.
-Polar molecules dissolves in Polar solvents 2. Carboxylic Acids – can
and vice versa. deprotonated by both weak
(Sodium bicarbonate) and strong
Polarizability of a Compound – atom’s
bases (NaOH) to give more polar,
ability due to external interference, to
water soluble salts.
distribute its electron density unequally.
3. Water Solubility of Phenols –
Polarization coincides with the interaction
phenols are weak acids and can
between electrons and the nucleus.
deprotonated by strong bases to
- Branching in the structure allows give polar and water-soluble salts.
the boiling point to decrease Weak acids do not deprotonate
because of less surface area them.
present. Thus, increasing the 4. Water Solubility of Amines –
solubility. Amines are bases and can be
protonated by an acid (HCl) to give
Determination of Solubilities more polar and water-soluble salt.
1. Water Solubility – Mixing
vigorously after adding portions of
water. Record as soluble if the ELEMENTAL ANALYSIS BY SODIUM
compound dissolves completely. FUSION
Solid samples, powder all solid
- Elemental Analysis – test for
samples to increase its rate of
detecting the presence of elements
dissolving. If it is insoluble after
in a compound. Use to determine:
mixing, apply heat then cool the
Molecular formula, structure,
mixture to room temp to avoid
Functional groups present,
super saturation.
Chemical reactivity of compounds.
2. Testing with Litmus Paper – If
both litmus paper turn red, the Sodium fusion – Sodium is ionically bonded
solubility class of the sample is SA. to N, S, and X (halides) to convert the
If both litmus paper turns blue, the covalent bonds.
solubility class of the sample is SB.
- CHANGE IN COLOR AND
3. Ether Solubility – Mix by shaking
PRECIPITATE FORMED MUST BE
vigorously after adding portions of
OBSERVED.
diethyl ether.
4. Aqueous Acid or Base – Addition
1. TEST FOR SULFUR:
of NaOH, Sodium bicarbonate, HCl
a. Add small portion of sodium
solution. Presence of cloudy
fusion. Acidify the solution
neutralized filtrate indicate that it is
by acetic acid (Sodium
soluble.
Nitroprusside Test)
5. Concentrated Acid – The
b. Add few drops of lead
phenomena with the reaction in
acetate (Lead Acetate
concentrated acid is to produce heat
Test)

ESPIRITU, Paul Robert D. BSCHEM 2-1

 c. FORMATION OF BLACK double and triple bonds which can
PRECIPITATE will reacts to acid to form carbocations.
determine the compounds - Saturated hydrocarbons (alkanes)
contain SULFUR. are not reactive as others.
1. Solubility Test in Water –
2. TEST FOR NITROGEN: observation of miscibility. A sample
a. Addition of Lassaigne’s was immiscible if layers are formed.
extract. 2. Solubility Test in Ligroin – same
b. Add freshly Ferrous sulphate with the procedure of water and
c. Heat the solution determination of miscibility.
d. Add Ferric chloride 3. Solubility Test in conc.HCl –
e. Add concentrated HCl same with the procedure for the
f. BLUE COMPLEX solution first 2 solubility test.
must be formed.
Ignition Test for Hydrocarbons:
g. Ammonia odor/RED
performed to identify the presence of
LITMUS TURNS TO BLUE
Carbon, oxygen and unsaturation of the
(BASIC SOLUTION)
sample.
3. TEST FOR OXYGEN: - Degree of luminosity of the sample
a. Indicator used: Ferrox strip can be assessed by the presence of
paper. yellow flame.
b. POSTIVE RESULT FOR - NON-AROMATIC COMPOUND
OXYGEN: ORANGE TO RED PRODUCES BLUE FLAME/NO
TO VIOLET COLORATION. BLACK UNBURNED (DUE TO THE
PRESENCE OF OXYGEN) – LOW
4. TEST FOR HALOGENS: PERCENTAGE OF CARBON.
a. Addition of silver nitrate (SATURATED HYDROCARBONS).
solution formed precipitate - AROMATIC COMPOUND
with halide content. PRODUCES YELLOW
b. FOR CHLORINE: WHITE FLAME/BLACK BURNED
PRECIPITATE PARTICLES – HIGH PERCENTAGE
c. FOR BROMINE: OF CARBON PRESENT
CREAM/PALE YELLOW (UNSATURATED HYDROCARBONS).
PRECIPITATE
d. FOR IODINE: YELLOW
PRECIPITATE Test for Aromatic Ring for
Hydrocarbons: aromatic rings undergo
substitution reaction with Bromine which is
slower than bromine addition to an alkene
GROUP 2 – HYDROCARBONS
or alkyne (requires catalyst). Iron (III)
Solubility Test: Hydrocarbons are non- bromide works well as catalyst.
polar compounds. They are not soluble in
Baeyer’s Test (Permanganate Test) for
water and dissolves in organic solvents like
Hydrocarbons: to determine the
ligroin.
unsaturation of hydrocarbons.
- Unsaturated hydrocarbons (alkenes
Examples of unsaturated carbons groups
and alkynes) are very reactive
are alkenes and alkynes.
towards sulfuric acid or un other
sources of H+ due to presence of

ESPIRITU, Paul Robert D. BSCHEM 2-1

Functional groups that can be oxidized are
aldehydes and some alcohols.
Uses a potassium permanganate that is
deep purple in color that will turn to a
brown precipitate upon reduction.
Permanganate ions cannot react with
aromatics. Thus, decolorization of the pink
color of KMnO4 indicates the unsaturation
of the solution. Positive Result: Brown in
color with precipitate. Negative result:
Pink in color without precipitate.
Classification Tests for Alkyl Halides
1. Alcoholic Silver nitrate test:
a. Proceeds via SN1
mechanism. Ethanol acts as
nucleophile because nitrate
ions are poor nucleophile.
Thus, silver nitrate is
sensitive enough to initiate
with small concentration of
halides ions.
b. Order of reactivity: 3 alkyl
halides > 2 alkyl halides
(perform in hot bath to
proceed). Thus, primary
alkyl halides do not react at
all because it does not form
stable carbocation at all.
c. Positive Results: Acidic
solution, white/cloudy
precipitate occur.
2. Sodium Iodide Test for Alkyl
chloride and bromides
(Finkelstein Test):
a. Proceeds via SN2
mechanism. Uses sodium
iodide in acetone as a
solvent. Precipitation of NaI
and NaBr in the acetone
must occur.
b. Order of Reactivity: 1 alkyl
halides > 2 alkyl halides.
Thus, tertiary alkyl halides
give no reaction because of
ESPIRITU, Paul Robert D. BSCHEM 2-1
the steric hindrance of the
molecule.
c. Positive Result: Appearance
of white cloudiness.
3. Beilstein Test for Alkyl Halides:
a. Confirms the presence of a
halogen in solution but does
not distinguish between
chlorine, bromine or iodine.
b. Copper oxide reacts with the
organic halide to produce a
copper halide compound that
gives a blue-green color to
the flame.
c. Positive result: green flame
produce (but short-lived and
faint)
GROUP 3 – CLASSIFICATION TESTS FOR
ALCOHOLS AND PHENOLS.
Solubility Test: generally, water solvates
alcohols with less than or equal to 5C atoms
as the oxygen hydrogen bond with water.
Miscibility can be observed if the alcohol
was soluble with water.
Acidity Test: Phenols are more acidic
than alcohols.
- Stability of the Conjugate base tells
as a key factor in determining
acidity of molecules.
- Alcohols where the conjugate base
is resonance stabilized will be more
acidic. That is why phenols
conjugate base are more stable
than alcohols connected to sp3
hybridized. Thus, more acidic.
- Presence of Electron Withdrawing
Group (such as F, Cl) stabilizes the
conjugate base of an alcohol. Thus,
more acidic.
- Conjugate base = Alkoxide ion.
(More stable alkoxide, more acidic)
- Order of Acidity strength of
Alcohols: 1 alcohols > 2 alcohols >3
alcohols.
 Acidity of Phenols: Most phenols are
weaker acids than carboxylic acids but
stronger acids than alcohols.
1. Litmus Test: litmus paper change to
red color indicates the presence of
Phenolic group.
Lucas Test: test to distinguish the alcohols
if its primary, secondary and tertiary
alcohols based on their reactivity with
hydrogen halide. (Use of Lucas Reagent –
Solution of concentrated HCl with Zinc
chloride)
a. Proceeds via SN1 mechanism in
which zinc chloride makes the OH as
a better leaving group leads to
formation of carbocation. Thus, Cl
ions acts as nucleophile to form
alkyl chloride.
b. In Primary alcohols: NO
REACTION OCCUR. No turbidity
or cloudy solution since it
proceeds via SN1.
c. In Secondary alcohols: have
TURBIDITY AND CLOUDY
SOLUTION AFTER 3-5 MINS. In
room temp, heating in warm water
and shaking is necessary with
water-insoluble alcohols.
d. In Tertiary alcohols: Turbidity
or Cloudy solution will appear
INSTANTLY at room temperature.
e. PHENOLS will not react with
Lucas Test, for it requires the
formation of a carbocation.
Jones Oxidation (Chromic acid test):
employs CrO3, H2SO4, and acetone as
reagent. A test for polar functional groups
like aldehydes, primary and secondary
alcohols. Tertiary alcohols give negative
results.
a. Cr3+ is a strong oxidizing agent
which oxidized aldehydes, primary
and secondary alcohols.
b. Positive result: giving off a blue-
green precipitate. Orange solution
leads to negative results.
ESPIRITU, Paul Robert D. BSCHEM 2-1
c. Water rinses the chromium residue
better than acetone.
Bromination: test based on addition of
bromine water to a phenol solution in water
to form 2.4.6-tribromophenol.
a. Orange colored bromine water is
added to a solution of phenol in
water, it gives off white
precipitate of 2,4,6 –
tribromophenol.
b. In resonance structure of
phenol, in 2,4, and 6 carbon, there
is a negative charge formed. Thus,
electrophilic aromatic substitution
of bromine attacks these sites.
c. Alcohols do not react with
bromine water as it does not form
resonance structure unlike phenols.
d. Alcohols will not form alkyl
halides unless the OH group is
converted into good leaving group.
Ferric Chloride Test: For PHENOLS; use
to identify the presence of phenol in the
sample. The sample will be dissolved in
water and will be reacted with a ferric
chloride solution.
a. If phenol is present in the sample,
dark colored complex will be
formed (violet, red, blue or
green).
b. Ferric ion will form complex to
phenoxide ions. Thus, H from the
OH will bond to Cl to form HCl.
c. Neutral Ferric chloride solution must
have in performing the test to avoid
acid-base neutralization and
formation of precipitate from a salt.
Otherwise, identification of phenol
will not happen.
CLASSIFICATION TEST FOR
ALDEHYDES AND KETONES:
1. DNPH TEST (2,4-
Dinitrophenylhydrazine):
 a. Red-orange powder which is results lead to clear solution
commonly a solution with and no precipitate formation
methanol + sulfuric acid even after heating and
(Brady’s reagent). agitating.
b. Aldehydes and ketones bond e. LIMITATIONS: CAN ALSO
the same to DNPH forms DETECT ALPHA-HYDROXY
intensely colored KETONES. Thus, Tollen’s
precipitate (yellow, reagent is dangerous if not
orange or red). neutralized.
c. Aromatic carbonyls give
red precipitates, aliphatic 3. Schiff’s Test: chemical test to
carbonyls give more determine the presence of
yellow color. aldehydes in a compound. Done by
d. Positive results: immediate reacting the analyte with a small
formation of color and quantity of a Schiff reagent.
significant amount of solids. a. Formation of magenta to
Absence of precipitate purple color upon the
and transparent yellow addition of analyte confirms
orange solution leads to the presence of aldehydes.
negative result. b. Colorless is a negative
e. LIMITATION: CANNOT result, thus no aldehydes
DIFFERENTIATE BETWEEN present in the analyte.
ALDEHYDES AND KETONES
4. Benedict’s Test: use to confirm
2. Tollen’s Test (Silver Mirror the presence of reducing sugars in
Test): use to distinguish between analyte. (Simple carbohydrates)
aldehydes and ketones. Takes contain free ketone or aldehyde can
advantage in manner of aldehydes be checked with this test.
because it is readily oxidizes while a. Benedict’s solution:
ketones do not. mixture of Sodium citrate,
a. Use of Tollen Reagent – sodium carbonate, and
colorless, basic, aqueous copper (II)sulfate
solution. Due to its short pentahydrate.
shelf life, it must be freshly b. the aldehyde of the sugar
prepared. gets oxidizes into a
b. Two-step procedure: 1st, carboxylic acid. When
additional of silver nitrate cuprous ions form copper
mixed with NaOH to form oxide, it precipitates as a
brown silver (I) oxide. 2nd, brick-red colored compound.
dropwise addition of c. BLUE – NONE
ammonia to form soluble GREEN YELLOW PPT –
complex with silver (I) oxide. TRACES OF REDUCING
c. Presence of Aldehydes in SUGAR
compound makes the ORANGE – MODERATE
complex reverts to AMOUNT OF REDUCING
elemental silver. Aldehydes SUGAR
becomes carboxylic acid. BRICK RED PPT – LARGE
d. Positive result: formation AMOUNT OF REDUCING
of mirror silver. Negative SUGARS.

ESPIRITU, Paul Robert D. BSCHEM 2-1

 d. LIMITATIONS: TEST
CANNOT TEL WHAT TYOE OF
MOLECULE IT TEST. Thus,
this test is qualitative and
not quantitative.
5. Iodoform Test: useful test to
identify the presence of these
methyl ketones or acetaldehyde in
compound. Iodine and sodium
hydroxides are reagents added to
compound. Thus, reaction of Iodine
and methyl ketones gives yellow
precipitate and antiseptic smell.
a. In the reaction, it produces
triiodomethane (iodoform)
and the salt of an acid.
b. Dark color of the solution
fades to yellow color.
c. Positive result: pale-yellow
precipitate of iodoform
form.
6. Bisulfite Test: useful to confirm
the presence of aldehydes and some
ketones. Use of sodium hydrogen
sulfite, (sodium bisulfite).
a. Aldehyde and methyl
ketones react with reagent
to form water-soluble
crystalline products.
b. Positive result: Has white
crystalline precipitate
formation.
c. Limitations: WORKS WITH
METHYL KETONES ONLY.
Bulky groups attached to the
carbonyl group gets in the
way of the reaction.
GROUP 4 – CLASSIFICATION TEST FOR
CARBOXYLIC ACIDS AND ACIDS
DERIVATIVES.
Esterification: ester formed when
carboxylic acid is treated with alcohols. This
reaction is called the Fischer
esterification.
ESPIRITU, Paul Robert D. BSCHEM 2-1
a. The reaction is an equilibrium.
b. Ester formation is favored when a
large excess alcohol is used as
solvent.
c. Mechanism: protonation by acid-
base reaction, 1,2-addition of
alcohol, proton transfer, 1,2-
elimination of water then
deprotonation by acid again.
Ester Test: addition of ethyl alcohol and
concentrated sulfuric acid. Carboxylic acid
reacts with alcohol in the acidic medium to
produce fruity smelling compound called
ESTER.
Ferric chloride Test for Carboxylic
acids: used for identification of phenols in
a sample. In case of testing for carboxylic
acid, the solution should be made neutral
first the acid before performing the test.
a. Phenolphthalein indicator is used
turn pink. Addition of dilute
ammonia until it is basic.
b. Proceeds via Substitution reaction.
c. After the odor of ammonia
disappears and neutralizing the
acid, let it cool and add ferric
chloride solution to acid.
d. Results: Formic and Acetic acid (red
solution), Succinic and Benzoic acid
(light brown precipitate to form),
Salicylic acid (violet solution),
Oxalic, Tartaric, Citric and Lactic
acid (no notable changes).
Hydroxamic Acid Test for Esters: it is
related to the phenol test. Compounds with
high enolic character can give a colored
complex with the Fe3+.
- Preliminary test is performed to see
if carbonyl compound produces
enough enol to form colored
complex to prevent false positive
result.
- Ferric hydroxamate is a test for the
ester functional group. Esters
heated with hydroxylamine
produces hydroxamic acids which
 form colored complex. (Dark
maroon color) with Fe3+.
- Additional of ethanol, HCl, and
Ferric chloride solution to analyte
for preliminary test.
Classification Tests for Amines
Basicity Test: amines are functional
groups being referred to as Lewis base due
to its capacity to donate electron pair.
- 2 TYPES OF AMINE: Alkyl and
Aromatic. This compound can be
distinguished using basicity test.
- For alkyl amines, higher pH
level.
- For aromatic amines, lower pH
level.
Hinsberg Test: chemical test that can
distinguish between the primary,
secondary and tertiary amines. Thus,
hisnberg reagent is used to produce the
amine.
a. Amine in the reactions acts as
nucleophile that attacks the
electrophilic molecule
(benzenesulfonly chloride)
b. Based upon sulfonamide formation.
As an amine reacts with the
benzenesulfonly chloride, it forms
whether primary or secondary
amine. Tertiary amines do not
form stable sulfonamides.
c. Sulfonamide that is soluble in NaOH
forms primary amine. Thus, it forms
only single layer
d. Sulfonamide that is insoluble in
NaOH forms secondary amine.
Thus, it forms double layer.
e. Proceeds via addition-elimination
reactions.
Nitrous Acid Test: nitrous acid reacts with
aliphatic amines that provides a useful test
for distinguishing the primary, secondary
and tertiary amines.
ESPIRITU, Paul Robert D. BSCHEM 2-1
- The amine would be acidified with
HCl and solution of sodium or
potassium nitrite is added.
- The acid and the nitrite form nitrous
acid which then reacts with amine.
a. Positive results: For primary
amine, gives of nitrogen gas
which is seen as bubbles. For
secondary amines, yellow oily
nitrosamine, no gas was
evolved. For tertiary amines,
forms soluble nitrite salts, no
gas and yellow liquid.
Ramini and Simon Tests:
Ramini – differentiate between primary
and secondary aliphatic amines.
1. Acetone and Sodium nitroprusside
in water. (Acetone used should be
free from acetaldehyde).
2. Positive result: the solution turns
color red. Violet color develops.
Simon – used to determine the presence
of secondary amines (diethylamine,
morpholine, piperidine, piperazine.)
1. Acetaldehyde and Sodium
nitroprusside in water.
2. Positive result: the solution
should develop blue-green
color.
Quinhydrone Test: useful test for
classifying amines as primary, secondary,
or tertiary. It distinguishes amines through
color change.
1. Aliphatic Amine: 1 – violet, 2 – rose,
3 – yellow
2. Aromatic: 1 – rose, 2 – amber, 3 –
yellow.
3. LIMITATIONS: Will not work for
diaminobenzenes or nitro-
substituted aromatic amines. Thus,
this test should be run in
conjunction with basicity test IR
spectrum that shows whether the
amine is aliphatic/alkyl or aromatic.
ESPIRITU, Paul Robert D. BSCHEM 2-1