CHEMISTRY LABORATORY (CHEM LAB) 1ST SEMESTER

LABORATORY EXPERIMENT 1 -11

EXPERIMENT 7 PHOSPOROUS: (Upon oxidation, phosphorous

changes to phosphate, which forms a yellow
COMPOSITION OF MOST ORGANIC COMPOUNDS
precipitate with ammonium molybdate)
I. PURPOSE: To recognize the presence elements
To a small amount of albumin in a test tube add
found in organic compounds
approximately 1 mL of concentrated nitric acid. Boil
II. APPARATUS: Erlenmeyer Flask, stopper/cork, carefully until the solution becomes clear. Cool
Delivery Tube, Dropper, Bunsen Burner thoroughly and the add slowly about as much cold
water as you have liquid in the test tube. Add a small
III. MATERIAL: 5 grams Brown sugar, 5cc yeast amount of ammonium molybdate solution and warm
suspension, clear lime water Solution, 8N NaOH Sol, carefully.
solution of I2, Benedict Solution
AMMONIUM PHOSPHOMOLYBDATE (NH4)3 PO4
IV. PROCEDURE: 12MoO3 precipitate indicates the presence of
Carbon and Hydrogen: (Organic compounds are phosphorous.
frequently inflammable and when heated take fire or Equation:
char)
3NH4 + 12M0O4- + PO4 3- + 24H+ = (NH4)3 PO4 .
Heat a very small amount of dry egg albumin in a test 12MoO3 + 12H20
tube.
HALOGENS: Heat Cu wire in the hottest portion of the
What collects in the upper and cooler portion of the flame until it does not give any color to the flame.
test tube? The hydrogen in the organic compound is Allow to cool. Moisten the wire with Chloroform in a
converted into water which deposits as moisture on test tube and hold the wire again in the flame.
the upper & cooler portion of the test tube.
What is the color of the flame? GREEN
Continue heating until there is no further change. The
charring indicates the presence of CARBON while the What is responsible for this color? DECOMPOSITION
formation of water indicates the presence of OF COPPER HALLIDE
HYDROGEN.
What is the name of the test? BElLSTEIN TEST
NITROGEN: (Organic compounds containing nitrogen
ALIPHATIC HYDROCARBONS
evolve ammonia upon being heated with soda lime).
Methane is formed by the decomposition of organic
Mix in a mortar and pestle ½ grams of urea with 1
material, such as dead leaves, in stagnant marshes,
gram of soda lime. Pour the mixture into a dry test
hence the name marsh gas. Methane is a constituent
tube and heat gently. Observe the odor of the gas
of coal gas, natural gas and of petroleum. It is called
evolved. Hold a piece of red litmus paper at the mouth
by the miner’s “firedamp”. The digestion of certain
of the test tube.
types of food in the body leads to the production of
What gas turned the litmus paper blue? AMMONIA methane, which may at times constitute as much as
(NH3) [basic] 50% of the intestinal gases

SULFUR: (Loosely combined sulfur after heating with Methane may be prepared in the laboratory
sodium hydroxide forms sodium sulfide which gives a by using soda lime and anhydrous sodium acetate. It is
black precipitate with lead acetate). collected by water displacement.

To 2mL of dilute sodium hydroxide in a test tube, add Acetylene, the first member of the alkyne series has a
a very small amount of egg albumin. Heat for a minute triple bond. It is commonly prepared in the laboratory
or more, cool the test tube in running water and add a by the action of water on calcium carbide.
few drops of lead acetate.
CaC2 + 2H2O -------→ H-C (triple bond) C-H + Ca
What is the color of the precipitate? BLACK (OH)2

Give the name and formula of the precipitate. LEAD It is very reactive chemically, forming addition
(||) SULFIDE (PBS) products like ethylene. Acetylene exhibits a chemical
property in which its hydrogen atoms are replaceable
Equation: by metals (silver and copper). This serves to
(CH3 CoO)2 Pb + Na2S = Pbs + 2CH3 CoONa differentiate olefins and acetylene hydrocarbons that
carry at least one acidic hydrogen.
Black Sodium acetate
Acetylene is a colorless, odorless gas which is slightly Acetylene + Bromine water → 1, 1, 2, 2 –
soluble in water. tetrabromoethane (colorless to yellowish soln.)

3. Add two drops of alcoholic iodine to 1mL of

EXPERIMENT 8 hexane and to acetylene.

PROPERTIES OF ALKANES AND ALKYNE Observations: No reaction, Iodine is the least

Reactive Orange solution
I. PURPOSE:
Hexane = C6 H14 + I2
II. APPARATUS:
Acetylene = HC (triple bond) CH + 12
III. MATERIAL:
4. Ignition Test for Alkane: (Hexane Only)
IV. PROCEDURE:
Take out the stopper of the fourth vial and
A. Preparation of Acetylene gas
immediately place the mouth of the test tube over
Set up a gas generator for the reaction of calcium a flame. Note the color of the flame.
carbide and water. Place the calcium carbide in a ORANGE/LUMINOUS.
distilling flask and by means of the medicine
Equation:
dropper; allow the water to fall, drop by drop,
upon the carbide. Let a few bubbles of gas escape 2C6 H14 + 19O2 → 12CO2 + 14H2O
first and ensure that no air is left in the apparatus.
Collect four vials of the gas by water
displacement. 5. Formation of Cuprous acetylide: Acetylene
only
CAUTION: Acetylene is very combustible, keep
away all flames. Add 5 mL of ammoniacal solution of cuprous
chloride into a vial that contains acetylene. Note
Write the equation of the above reaction:
the color of the precipitate
CaC2 + 2H2O --→ HC (triple bond) CH + Ca (OH)2
Observations: Chocolate Brown Precipitate
B. Properties alkane and alkyne: →Cuprous Acetylide
1. Baeyer’s test for Unsaturation.
Acetylene is a colorless, odorless gas which is
Add 1 mL of potassium permanganate solution to slightly soluble in water
the vial of 1mL hexane, stopper and shake. Repeat
Equation:
the procedure to a vial that contain acetylene gas.
Record your observations. HC (triple bond) CH + Cu2 Cl2 + 2NH4OH → CuC
(triple bond) CCu+2NH4Cl + 2H2O
Observations: Formation of Brown Precipitate
(Manganese Dioxide) on Acetylene and potassium EXPERIMENT 9
permanganate Hexane and potassium
permanganate separates, no reaction, immiscible. FERMENTATION

EQUATIONS: 3HC= CH + 10KMnO4 +2H2O --→ I. PURPOSE: To observe the chemical process by
10MnO4 (down arrow) + 6Co2 + 10KOH which molecules such as glucose are broken
down anaerobically.
2. Add 1 mL of bromine water to the vial of 1 mL
hexane, stopper, shake and expose it under II. APPARATUS: Erlenmeyer Flask, stopper/cork,
sunlight. Repeat the procedure to a vial that Delivery Tube, Dropper, Bunsen Burner
contain acetylene gas. (no need to expose III. MATERIAL: 5 grams Brown sugar, 5cc yeast
under sunlight) Record your observations. suspension, clear lime water Solution, 8N NaOH
OBSERVEATIONS: Acetylene + Br2 = Yellow color Sol, solution of I2, Benedict Solution

Hexane + Br2 = Colorless & light yellow IV. PROCEDURE:

Give the names of the organic products of alkane Dissolve 5grams of brown sugar in 150 mL of hot
and alkyne. 1 bromohexane/ Hexyl - Bromide water in an Erlenmeyer flask and allow it to cool.
Add 5cc of yeast suspension. Mix thoroughly and
EQUATION: fit the flask with a stopper and a delivery tube
whose exit is placed in a tube with clear lime
HC (triple bond) CH + 2Br2 -> H2C2Br4
water solution. Observe the fermentation from
C6 H14 + Br2 → C6H13Br + HBr (Gas, pale yellow) time to time during the next day.
Hydrogen bromide
Decent and filter contents in the flask into a clean CH3 CH2 OH+CAC2 --> CH3 CH2 OH+HO(3 bonds)
container and perform the following tests on the CH + CA (OH)2
filtrate.
2. Test for water in Alcohol:
OBSERVATION AND EQUATIONS:
(Note: if the copper sulfate available is hydrous
Molds above, yeast below (blue) heat it strongly until it becomes anhydrous
(white)
Test tube has white calcium carbide
Place powdered anhydrous copper sulfate in each
C12 H22 + H2O= 2C6 H12 O6
of two recently dried test tubes. Add 2 mL of 95 %
2C6 H12 O= 4CH2 CH2 OH + O2 ethyl alcohol to one test tube and an equal
amount of the prepared anhydrous alcohol to the
1. Iodoform test (test for the presence of ethyl other.
alcohol)
Note: the difference in color between the two Add
To 1cc of the filtrate add 3 drops of 8 N NaOH 1 drop to water of the anhydrous alcohol.
solution, then dropwise a solution of I2 in KI until a
faintly yellow color persists. Warm the mixture at OBSERVATION:
about 60 0C and set aside for 5-10 mins.
➢ 95% of ethyl alcohol + CuSO4 --> Copper,
OBSERVATION: Yellow – Pale Yellow Precipitate - Sulfate turned blue
Yellow ➢ 100% of anhydrous alcohol --> Copper
sulfate remained white
EQUATION: ➢ 100% of anhydrous alcohol --> 1drop H2o
CH3CH2OH + 6NaOH + 4I2 -> HCoONa + 5NaI -->. Copper Sulfate turned blue with
+CHI3 + 5H20 brown ppt around it

2. Benedict's test (test for the presence of sugar) The change in color indicates? The presence of
Water
Add 1 cc of Benedict's solution to 1 cc of the
filtrate. Boil for 1 min and cool. EQUATION:

OBSERVATION: Pale Yellow – Blue → Green (95%) CH3CH2OH + CUSO4 --> CH3CH2OH +
CUSO4 5H2O
EXPERIMENT 10
(100%) CH3CH2OH + CUSO4 --> White Solid
REACTIONS OF ALCOHOLS AND PHENOLS CUSO4
I. PURPOSE: To observe the solubility of alcohols 3. Esterification:
relative to their chemical structure to understand
the different reactions of alcohol a. Mix in a test tube 1 mL each of ethyl alcohol and
acetic acid and a little less than 1 mL of
II. APPARATUS: Dry filter paper, Funnel, Cork, Test concentrated sulfuric acid. Warm in a water bath
tubes for 20 minutes. Then pour into 50 mL of cold
III. MATERIALS: Ethyl Alcohol, Calcium Carbide, water. Odor? PLASTIC BALLOON ODOR
Water, anhydrous copper sulfate, acetic acid conc EQUATION:
& Dilute Sulfuric acid, methyl alcohol, Salicylic
acid, Na OH Solution, iodine, isopropyl alcohol, CH3 CH2OH + CH3 COOH --> CH3 O=C-OCH2 CH3
test-butyl alcohol, Potassium dichromate + H2O

IV. PROCEDURE: b. Repeat (a) using 1 mL methyl alcohol, salicylic

acid and conc. sulfuric acid. Odor?
A. 1. Dehydration of Alcohol:
MINT (OIL OF WINTERGREEN) / Methyl Salicylate
Place about 10 mL of ethyl alcohol in a test tube.
Add 1 gram of calcium carbide. Cork the tube EQUATION:
loosely and warm at about 60 oC in water bath for CH3OH +C6H4OH COOH -->C6H4OH COOCH3 +
10 minutes. (During this time perform the other H2O
parts of the experiment)
4. Iodoform Test:
Cool the mixture and filter through a dry filter
paper and funnel into a recently dried test tube. To 4 drops of ethyl alcohol in 1 mL water, add 3
Cork and save the filtrate for (2) and (3). drops of 8 N NaOH solution. then dropwise a
solution of iodine in KI until a faint yellow color
EQUATION: persists. Warm the mixture in a water bath at
about 60 oC. Set aside for 5 - 10 minutes.
OBSERVATION: PROPERTIES OF ALDEHYDES AND KETONES

Iodoform = Yellow Precipitate was formed & had I. PURPOSE: To acquainted with the diff properties
medical odor of Aldehydes & ketones

EQUATION: II. APPARATUS: Clay Shield, Bunsen burner,

dropper
CH3 CH2OH + 4I2 + 6NaOH --> CHI3 + H CoONa +
5NaI + H2O III. MATERIALS: 1 mL Schiff’s Solution, formalin,
Benzaldehyde, Acetone conc. Sulfuric acid, gelatin
5. Oxidation:
Sheet, hot water, Ammoniacal sol of silver of
Put 1/2 mL of ethyl alcohol, isopropyl alcohol and nitrate, Fehling’s solution 10 % of NaOH Iodine
tert-butyl alcohol in 3 separate test tubes. To each solution
add 5 drops pf potassium dichromate and 5 drops
IV. PROCEDURE:
of dilute sulfuric acid. Warm in a water bath. Note
the color and odor each solution. Compare and 1. Schiff's Test:
find out which alcohol is easily oxidized.
In each of 3 test tubes place 1 mL of Schiff's
OBSERVATION: solution (colorless). To one tube add a few drops
formalin, to the second, a few drops of
➢ Isopropyl --> Blue
benzaldehyde and to the third, a few drops of
➢ Ethyl --> Blue green
acetone.
➢ Tert - butyl --> Brownish Yellow
OBSERVATION: Formalin solution become pink,
EQUATION:
Benzaldehyde formed cloudy bubble, Acetone is
CH3 CH2OH +K2 CR2 O7 + H2SO4 -->K2 SO4 + CR2 colorless
(SO4)3 + CH3 COOH + H2O
2. Resorcinol Test:
CH3 CHOHCH3 + KrCr2O7 + H2 SO4 --> K2 SO4 +
To 1/2 mL formalin in a test tube, add a drop of
Cr2 (SO4)3 + CH3 COCH3 +H2O
0.5% Resorcinol solution and mix well. Incline the
Tert - butyl did not oxidized test tube and introduce 1/2 mL of concentrated
sulfuric acid by means of a dropper so that the
6. Replacement of the Hydroxyl Group with acid will form a layer at the bottom. Note the color
Halogen: Lucas Test. at the junction of the two layers.
Place 1/2 mL each of ethyl alcohol, isopropyl OBSERVATION: Upper layer is clear
alcohol and tert-butyl alcohol in separate test
tubes. Add 3 mL of HCI and ZnCI2 reagent to each. Upper – White Precipitate
Warm in a water bath to 26 - 27 oC. Stopper the
Middle – Red Flocculent precipitate
tubes. shake the mixture and allow to stand. A
cloudiness in the solution is the first sign of a Bottom – pale yellow
reaction. Observe the tubes at each of the
3. Action of Formaldehyde on Proteins:
following periods; 1) immediately after mixing; 2)
after standing 5 minutes; 3) after standing 1/2 Mix 1 mL of formalin and 1 mL of water in a test
hour, Observe the relative rates of reaction. tube and shake the mixture. Place a strip of gelatin
sheet in this solution such that about 1/2 of the
OBSERVATION:
sheet projects above the surface of the solution.
Ethyl was fast to react |CLEAR|CLEAR Allow it to stand for 15 to 20 minutes. Remove the
sheet and test its solubility in hot water. Observe
Isopropyl was second to react
the portion which did not come in contact with
|CLEAR|CLOUDY
the solution.
Tert-butyl was the first to react
OBSERVATION: Portions of gelatin that got
|CLOUDY|CLOUDY
exposed to formalin hardened While the portion
EQUATION: that was not exposed remain soft & turn into jelly

CH3 CH2OH + HCI --> CH3 CH2 CI + H2O 4. Silver Mirror Test or Tollens’s Test:

CH3 CHOHCH3 + HCI --> CH3 CH3-CHCI + H2O Place 2 mL of an ammoniacal solution of silver
nitrate in each of 3 clean and dry test tubes. To
CH3 OH3-C-CH3-OH + HCI -->CH3 CH3-CHCI + one add 5 drops formalin, to the second 5 drops
H2 O of benzaldehyde and to the third, 5 drops of
EXPERIMENT 11 acetone. Agitate the mixture in each tube
thoroughly then warm in the water bath. After the
mirror has formed. throw out the contents of the EXPERIMENT 12
tube and rise with distilled water.
PROPERTIES OF CARBOXYLIC ACID and SALICYLIC
OBSERVATION: Tube w/ formalin = Formation of ACID

metallic Silver, Tube w/ benzaldehyde = White |. PURPOSE: To learn physical properties of Carboxylic
solution, Yellowish upper, cloudy, Tube w/ Acid and the different reactions of Salicylic Acid
Acetone no reaction
||. APPARATUS: Test tubes, droppers, breaker, mortar &
EQUATION: pestle, Bunsen burner, Clay Shield, Wire gauze, funnel,
filter paper
H-CHO + 2Ag(NH3)2OH + H2O -> H-COOH + 2Ag
|||. MATERIALS: Acetic Acid, Benzoic Acid, Stearic Acid,
+ 4NH3 + 2H2O
Formic Acid, Oxalic Acid, 0.5% Potassium
C6H5CH + 2Ag(NH3)2OH + H2O -> C6H6COOH + permanganate, water, Salicylic Acid, Ferric Chloride
2Ag + 4NH3 +H2O |V. PROCEDURE: Ferric Nitrate, Bromine water, Million’s
Reagent, Soda lime, Methyl Alcohol, conc. Sulfuric Acid,
(CH3)2CO + 2Ag (NH3)2OH -> NO REACTION
1. SOLUBILITY OF CARBOXYLIC ACID IN WATER:
5. Fehling's Test:
Test the solubility in water of the following acids; acetic,
Place 1 mL of Fehling's Solution in each of 3 test benzoic, and stearic acid. Use 3 drops of liquid (or a
tubes. To one add a few drops of formalin, to the pinch if solid) to 3 mL of water. Account for the large
second, a few drops of benzaldehyde and to the observed differences in solubility between acetic acid
third, a few drops of acetone. Mix the contents in and stearic acid
each tube thoroughly and warm in a water bath.
Why would stearic acid be expected to show a lower
OBSERVATION: Test tube w/ formalin blue color solubility in water? Has long hydrocarbon chain, is
solution turns brick red precipitate, Test tube w/ hydrophobic and repels the water molecules to the
benzaldehyde = remains blue, Test tube w/ extent that the compound is insoluble in water.
Acetone = No reaction
2. ACTION OF AN OXIDIZING AGENT ON THE
EQUATION: CARBONYL GROUP:

H-CHO + Cu (OH)2 -> H-COOH + Cu2O +H2O Place 5 drops of acetic, formic, benzoic and oxalic acid
in four separate test tubes and add 1 mL of 0.5%
NO REACTION potassium permanganate to each tube. Heat the four
test tubes in a water bath, and note if any reduction of
NO REACTION
the permanganate occurs.
6. Auto-Oxidation of Benzaldehyde.
Write the equations involved.
(DEMONSRATION)
NR for Acetic and Benzoic Acid
Place a few drops of benzaldehyde to a watch HCOOH + KMNO + 6H + → 6CO2 2H2O + 2Mn+ 2 +KOH
glass. Expose to the atmosphere. Observe the (COOH)2 + KMNO+ + 6H+ → 4H20 + 10CO2 + 2Mn+2 +
KOH
formation of a white crystals.

OBSERVATION: A fine White crystalline was 3. PREPARATION OF SALICYLIC ACID SOLUTION:

formed (Benzoic Acid)
Add 15 mL of water to 0.1 gram of salicylic acid and
EQUATION: shake the solution for a few minutes, filter the solution
and divide the filtrate into three portions, and use them
C6H5COH -> C6H5COOOH -> C6H5COOH as stated below:

7. Iodoform Test for Methyl Ketones: a. Reaction with Ferric ions.

Place 2 drops of acetone in a test tube and add 8 To the first five mL portion of the prepared solution, add
drops of 10 % NaOH solution. Slowly add dropwise 1 or 2 drops of ferric chloride or ferric nitrate solution.
iodine solution until the liquid remains yellow.
Warm the tube in a water bath at 60 oC Note the Observation: Purple reaction after adding FecI3
color of the precipitate.
Equation: C6H4OH COOH + 3Br2 → ( C6H4OHCOO
OBSERVATION & EQUATIONS: before heating the )3 + 3HBr + CO2
solution was yellow. After heating, pale yellow
precipitate formed Iodoform b. Reaction with Bromine Water

To the second 5 mL portion of the prepared solution,

CH3COCH3 +4NaOH + 3I2 -> CH3COONa + CHI3 +
add a few drops of bromine water, a few drops at a time
3NaI + 3H2O
until a light yellow solution is obtained.

OBSERVATION:
The solution initially became translucent white to a faint complete, separate the aspirin crystals by filtration. Dry
yellow color. the crystals by pressing between filter papers. When
sufficiently dry, get the weight of the aspirin crystals.
EQUATION: Br
OH
C6H4OHCOOH + 3Br2 → +3HBr + CO2 Write the equation for the synthesis:
Br Br
c. Reaction with Million’s reagent. C7H6O3 + (CH3CO)2 O → Ca H8 O4 + CH3 COOH

To the last five mL portion of the solution prepared Weight of dry aspirin = 180. 157g/mol
solution, add 1 or 2 drops of Million’s reagent, and warm
the mixture. Observe the color of the precipitate. Calculate:

Observation: a. the theoretical yield

1 mole Apirin 180.157g Aspirin
0.0217 mole SA x x = 3.9 g
1 mole SA 1 mole Aspirin
Precipitate at the bottom and light – red colored
Aspirin
solution

b. the % yield
Equation: C6H4OH COOH + Hg N2 O6 → C6 H4 OH Actual Yield 3.0 g Aspirin
COOHg +2NO2 x 100 = x 100 = 76.9%
Theoretical Yield 3.9 g Aspirin

4. REACTION WITH SODA-LIME.

Grind in a mortar about 0.2 gram of salicylic acid with 2

grams of soda – lime, place the mixture in a dry test
tube and heat strongly. Notice the odor of the vapors
given off.

Observation:

When the mixture was heated, a paste – like odor was

produced
OH
NaOH H
Equation: C6 H4 OH COOH + CO2
CaO

5. ESTER FORMATION :

Place in a test tube about 0.1 gram of salicylic acid, add

15 – 20 drops of methyl alcohol and 1 mL of
concentrated sulfuric acid, and gently boil the mixture
for 1 – 2 minutes: then pour the mixture into about 20
mL of water, contained in a breaker. Notice the odor of
the diluted mixture.

Observation: The mixture produced a minty odor ( oil of

winter green )
H2SO4
Equation: CH3OH + C6 H4OHCOOH C 6 H4
OH COOCH3 + H20

EXPERIMENT 13
PREPARATION OF ASPIRIN

|. PURPOSE: To conduct a chemical reaction to produce

aspirin, to analyze the aspirin and estimate its purity
||. APPARATUS: Flask, long glass tubing, cork, Bunsen
burner, clay shield, wire gauze, funnel, filter paper,
|||. MATERIAL: Salicylic Acid, Acetic Anhydride, conc.
Sulfuric acid, water, ice,
|V. PROCEDURE:

Place 3 grams of salicylic acid in a flask and add 3 mL of

acetic anhydride. Add 3 drops of concentrated sulfuric
acid and attach a long glass tubing with a cork (serves
as an air condenser) and heat the flask in a water bath
for 10 to 15mins. Allow the flask to cool and add about
30 mL of ice water. Crystallize the aspirin by cooling
the flask in an ice bath. When the crystallization is