CHEMISTRY LABORATORY (CHEM LAB) 1 SEMESTER

Add a small amount of ammonium molybdate

ST
solution and
LABORATORY warm carefully. EXPERIMENT 1 -11
AMMONIUM PHOSPHOMOLYBDATE (NH4)3 PO4
EXPERIMENT 7 12MoO3 precipitate indicates the presence of phosphorous.

COMPOSITION OF MOST ORGANIC COMPOUNDS Equation:

I. PURPOSE: To recognize the presence elements found in 3NH4 + 12M0O4- + PO4 3- + 24H+ = (NH4)3 PO4 . 12MoO3 +
organic compounds 12H20

II. APPARATUS: Erlenmeyer Flask, stopper/cork, Delivery HALOGENS: Heat Cu wire in the hottest portion of the flame
Tube, Dropper, Bunsen Burner until it does not give any color to the flame. Allow to cool.
Moisten the wire with Chloroform in a test tube and hold the
III. MATERIAL: 5 grams Brown sugar, 5cc yeast suspension, wire again in the flame.
clear lime water Solution, 8N NaOH Sol, solution of I2,
Benedict Solution What is the color of the flame? GREEN

IV. PROCEDURE: What is responsible for this color? DECOMPOSITION OF

COPPER HALLIDE
Carbon and Hydrogen: (Organic compounds are frequently
inflammable and when heated take fire or char) What is the name of the test? BElLSTEIN TEST

Heat a very small amount of dry egg albumin in a test tube. ALIPHATIC HYDROCARBONS

What collects in the upper and cooler portion of the test tube? Methane is formed by the decomposition of organic material,
The hydrogen in the organic compound is converted into water such as dead leaves, in stagnant marshes, hence the name
which deposits as moisture on the upper & cooler portion of marsh gas. Methane is a constituent of coal gas, natural gas
the test tube. and of petroleum. It is called by the miner’s “firedamp”. The
digestion of certain types of food in the body leads to the
Continue heating until there is no further change. The charring production of methane, which may at times constitute as much
indicates the presence of CARBON while the formation of as 50% of the intestinal gases
water indicates the presence of HYDROGEN.
Methane may be prepared in the laboratory by using
NITROGEN: (Organic compounds containing nitrogen evolve soda lime and anhydrous sodium acetate. It is collected by
ammonia upon being heated with soda lime). water displacement.
Mix in a mortar and pestle ½ grams of urea with 1 gram of Acetylene, the first member of the alkyne series has a triple
soda lime. Pour the mixture into a dry test tube and heat bond. It is commonly prepared in the laboratory by the action
gently. Observe the odor of the gas evolved. Hold a piece of of water on calcium carbide.
red litmus paper at the mouth of the test tube.
CaC2 + 2H2O ------- H-C (triple bond) C-H + Ca (OH)2
What gas turned the litmus paper blue? AMMONIA (NH3)
[basic] It is very reactive chemically, forming addition products like
ethylene. Acetylene exhibits a chemical property in which its
SULFUR: (Loosely combined sulfur after heating with sodium hydrogen atoms are replaceable by metals (silver and copper).
hydroxide forms sodium sulfide which gives a black This serves to differentiate olefins and acetylene hydrocarbons
precipitate with lead acetate). that carry at least one acidic hydrogen.
To 2mL of dilute sodium hydroxide in a test tube, add a very Acetylene is a colorless, odorless gas which is slightly soluble
small amount of egg albumin. Heat for a minute or more, cool in water.
the test tube in running water and add a few drops of lead
acetate. EXPERIMENT 8

What is the color of the precipitate? BLACK PROPERTIES OF ALKANES AND ALKYNE

Give the name and formula of the precipitate. LEAD (||) I. PURPOSE:
SULFIDE (PBS)
II. APPARATUS:
Equation:
III. MATERIAL:
(CH3 CoO)2 Pb + Na2S = Pbs + 2CH3 CoONa
IV. PROCEDURE:
Black Sodium acetate
A. Preparation of Acetylene gas

Set up a gas generator for the reaction of calcium carbide

and water. Place the calcium carbide in a distilling flask
and by means of the medicine dropper; allow the water to
PHOSPOROUS: (Upon oxidation, phosphorous changes to fall, drop by drop, upon the carbide. Let a few bubbles of
phosphate, which forms a yellow precipitate with ammonium gas escape first and ensure that no air is left in the
molybdate) apparatus. Collect four vials of the gas by water
To a small amount of albumin in a test tube add approximately displacement.
1 mL of concentrated nitric acid. Boil carefully until the CAUTION: Acetylene is very combustible, keep away all
solution becomes clear. Cool thoroughly and the add slowly flames.
about as much cold water as you have liquid in the test tube.
Write the equation of the above reaction:
CaC2 + 2H2O -- HC (triple bond) CH + Ca (OH)2 EXPERIMENT 9

B. Properties alkane and alkyne: FERMENTATION

1. Baeyer’s test for Unsaturation.
I. PURPOSE: To observe the chemical process by which
Add 1 mL of potassium permanganate solution to the vial molecules such as glucose are broken down anaerobically.
of 1mL hexane, stopper and shake. Repeat the procedure
to a vial that contain acetylene gas. Record your II. APPARATUS: Erlenmeyer Flask, stopper/cork,
observations. Delivery Tube, Dropper, Bunsen Burner

Observations: Formation of Brown Precipitate III. MATERIAL: 5 grams Brown sugar, 5cc yeast
(Manganese Dioxide) on Acetylene and potassium suspension, clear lime water Solution, 8N NaOH Sol,
permanganate Hexane and potassium permanganate solution of I2, Benedict Solution
separates, no reaction, immiscible. IV. PROCEDURE:
EQUATIONS: 3HC= CH + 10KMnO4 +2H2O -- Dissolve 5grams of brown sugar in 150 mL of hot water
10MnO4 (down arrow) + 6Co2 + 10KOH in an Erlenmeyer flask and allow it to cool. Add 5cc of
2. Add 1 mL of bromine water to the vial of 1 mL yeast suspension. Mix thoroughly and fit the flask with a
hexane, stopper, shake and expose it under sunlight. stopper and a delivery tube whose exit is placed in a tube
Repeat the procedure to a vial that contain acetylene with clear lime water solution. Observe the fermentation
gas. (no need to expose under sunlight) Record your from time to time during the next day.
observations. Decent and filter contents in the flask into a clean
OBSERVEATIONS: Acetylene + Br2 = Yellow color container and perform the following tests on the filtrate.

Hexane + Br2 = Colorless & light yellow OBSERVATION AND EQUATIONS:

Give the names of the organic products of alkane and Molds above, yeast below
alkyne. 1 bromohexane/ Hexyl - Bromide Test tube has white calcium carbide
EQUATION: C12 H22 + H2O= 2C6 H12 O6
HC (triple bond) CH + 2Br2 -> H2C2Br4 2C6 H12 O= 4CH2 CH2 OH + O2
C6 H14 + Br2  C6H13Br + HBr (Gas, pale yellow) 1. Iodoform test (test for the presence of ethyl alcohol)
Hydrogen bromide
To 1cc of the filtrate add 3 drops of 8 N NaOH solution,
Acetylene + Bromine water  1, 1, 2, 2 – then dropwise a solution of I2 in KI until a faintly yellow
tetrabromoethane (colorless to yellowish soln.) color persists. Warm the mixture at about 60 0C and set
3. Add two drops of alcoholic iodine to 1mL of hexane aside for 5-10 mins.
and to acetylene. OBSERVATION: Yellow – Pale Yellow Precipitate -
Observations: No reaction, Iodine is the least Reactive Yellow
Orange solution EQUATION:
Hexane = C6 H14 + I2 CH3CH2OH + 6NaOH + 4I2 -> HCoONa + 5NaI +CHI3 +
Acetylene = HC (triple bond) CH + 12 5H20

4. Ignition Test for Alkane: (Hexane Only) 2. Benedict's test (test for the presence of sugar)

Take out the stopper of the fourth vial and immediately Add 1 cc of Benedict's solution to 1 cc of the filtrate. Boil
place the mouth of the test tube over a flame. Note the for 1 min and cool.
color of the flame. ORANGE/LUMINOUS. OBSERVATION: Pale Yellow – Blue  Green
Equation: EXPERIMENT 10
2C6 H14 + 19O2  12CO2 + 14H2O REACTIONS OF ALCOHOLS AND PHENOLS

I. PURPOSE: To observe the solubility of alcohols

5. Formation of Cuprous acetylide: Acetylene only relative to their chemical structure to understand the
different reactions of alcohol
Add 5 mL of ammoniacal solution of cuprous chloride
into a vial that contains acetylene. Note the color of the II. APPARATUS: Dry filter paper, Funnel, Cork, Test
precipitate tubes

Observations: Chocolate Brown Precipitate Cuprous III. MATERIALS: Ethyl Alcohol, Calcium Carbide,
Acetylide Water, anhydrous copper sulfate, acetic acid conc &
Dilute Sulfuric acid, methyl alcohol, Salicylic acid, Na
Acetylene is a colorless, odorless gas which is slightly OH Solution, iodine, isopropyl alcohol, test-butyl alcohol,
soluble in water Potassium dichromate

Equation: IV. PROCEDURE:

HC (triple bond) CH + Cu2 Cl2 + 2NH4OH  CuC A. 1. Dehydration of Alcohol:

(triple bond) CCu+2NH4Cl + 2H2O
Place about 10 mL of ethyl alcohol in a test tube. Add 1 Iodoform = Yellow Precipitate was formed & had medical
gram of calcium carbide. Cork the tube loosely and warm odor
at about 60 oC in water bath for 10 minutes. (During this
time perform the other parts of the experiment) EQUATION:

Cool the mixture and filter through a dry filter paper and CH3 CH2OH + 4I2 + 6NaOH --> CHI3 + H CoONa + 5NaI
funnel into a recently dried test tube. Cork and save the + H2O
filtrate for (2) and (3). 5. Oxidation:
EQUATION: Put 1/2 mL of ethyl alcohol, isopropyl alcohol and tert-
CH3 CH2 OH+CAC2 --> CH3 CH2 OH+HO(3 bonds) CH + butyl alcohol in 3 separate test tubes. To each add 5 drops
CA (OH)2 pf potassium dichromate and 5 drops of dilute sulfuric
acid. Warm in a water bath. Note the color and odor each
2. Test for water in Alcohol: solution. Compare and find out which alcohol is easily
oxidized.
(Note: if the copper sulfate available is hydrous (blue)
heat it strongly until it becomes anhydrous (white) OBSERVATION:

Place powdered anhydrous copper sulfate in each of two  Isopropyl --> Blue
recently dried test tubes. Add 2 mL of 95 % ethyl alcohol  Ethyl --> Blue green
to one test tube and an equal amount of the prepared  Tert - butyl --> Brownish Yellow
anhydrous alcohol to the other.
EQUATION:
Note: the difference in color between the two Add 1 drop
to water of the anhydrous alcohol. CH3 CH2OH +K2 CR2 O7 + H2SO4 -->K2 SO4 + CR2 (SO4)3
+ CH3 COOH + H2O
OBSERVATION:
CH3 CHOHCH3 + KrCr2O7 + H2 SO4 --> K2 SO4 + Cr2
 95% of ethyl alcohol + CuSO4 --> Copper, (SO4)3 + CH3 COCH3 +H2O
Sulfate turned blue
 100% of anhydrous alcohol --> Copper sulfate Tert - butyl did not oxidized
remained white 6. Replacement of the Hydroxyl Group with Halogen:
 100% of anhydrous alcohol --> 1drop H2o -->. Lucas Test.
Copper Sulfate turned blue with brown ppt
around it Place 1/2 mL each of ethyl alcohol, isopropyl alcohol and
tert-butyl alcohol in separate test tubes. Add 3 mL of HCI
The change in color indicates? The presence of Water and ZnCI2 reagent to each. Warm in a water bath to 26 -
EQUATION: 27 oC. Stopper the tubes. shake the mixture and allow to
stand. A cloudiness in the solution is the first sign of a
(95%) CH3CH2OH + CUSO4 --> CH3CH2OH + CUSO4 reaction. Observe the tubes at each of the following
5H2O periods; 1) immediately after mixing; 2) after standing 5
minutes; 3) after standing 1/2 hour, Observe the relative
(100%) CH3CH2OH + CUSO4 --> White Solid CUSO4 rates of reaction.
3. Esterification: OBSERVATION:
a. Mix in a test tube 1 mL each of ethyl alcohol and acetic Ethyl was fast to react |CLEAR|CLEAR
acid and a little less than 1 mL of concentrated sulfuric
acid. Warm in a water bath for 20 minutes. Then pour into Isopropyl was second to react |CLEAR|CLOUDY
50 mL of cold water. Odor? PLASTIC BALLOON
ODOR Tert-butyl was the first to react |CLOUDY|CLOUDY

EQUATION: EQUATION:

CH3 CH2OH + CH3 COOH --> CH3 O=C-OCH2 CH3 + CH3 CH2OH + HCI --> CH3 CH2 CI + H2O
H2O CH3 CHOHCH3 + HCI --> CH3 CH3-CHCI + H2O
b. Repeat (a) using 1 mL methyl alcohol, salicylic acid CH3 OH3-C-CH3-OH + HCI -->CH3 CH3-CHCI + H2O
and conc. sulfuric acid. Odor?
EXPERIMENT 11
MINT (OIL OF WINTERGREEN) / Methyl Salicylate
PROPERTIES OF ALDEHYDES AND KETONES
EQUATION:
I. PURPOSE: To acquainted with the diff properties of
CH3OH +C6H4OH COOH -->C6H4OH COOCH3 + H2O Aldehydes & ketones
4. Iodoform Test: II. APPARATUS: Clay Shield, Bunsen burner, dropper
To 4 drops of ethyl alcohol in 1 mL water, add 3 drops of III. MATERIALS: 1 mL Schiff’s Solution, formalin,
8 N NaOH solution. then dropwise a solution of iodine in Benzaldehyde, Acetone conc. Sulfuric acid, gelatin Sheet,
KI until a faint yellow color persists. Warm the mixture in hot water, Ammoniacal sol of silver of nitrate, Fehling’s
a water bath at about 60 oC. Set aside for 5 - 10 minutes. solution 10 % of NaOH Iodine solution
OBSERVATION: IV. PROCEDURE:

1. Schiff's Test:
In each of 3 test tubes place 1 mL of Schiff's solution H-CHO + Cu (OH)2 -> H-COOH + Cu2O +H2O
(colorless). To one tube add a few drops formalin, to the
second, a few drops of benzaldehyde and to the third, a NO REACTION
few drops of acetone. NO REACTION
OBSERVATION: Formalin solution become pink, 6. Auto-Oxidation of Benzaldehyde.
Benzaldehyde formed cloudy bubble, Acetone is colorless (DEMONSRATION)
2. Resorcinol Test: Place a few drops of benzaldehyde to a watch glass.
To 1/2 mL formalin in a test tube, add a drop of 0.5% Expose to the atmosphere. Observe the formation of a
Resorcinol solution and mix well. Incline the test tube and white crystals.
introduce 1/2 mL of concentrated sulfuric acid by means OBSERVATION: A fine White crystalline was formed
of a dropper so that the acid will form a layer at the (Benzoic Acid)
bottom. Note the color at the junction of the two layers.
EQUATION:
OBSERVATION: Upper layer is clear
C6H5COH -> C6H5COOOH -> C6H5COOH
Upper – White Precipitate
7. Iodoform Test for Methyl Ketones:
Middle – Red Flocculent precipitate
Place 2 drops of acetone in a test tube and add 8 drops of
Bottom – pale yellow 10 % NaOH solution. Slowly add dropwise iodine
3. Action of Formaldehyde on Proteins: solution until the liquid remains yellow. Warm the tube in
a water bath at 60 oC Note the color of the precipitate.
Mix 1 mL of formalin and 1 mL of water in a test tube
and shake the mixture. Place a strip of gelatin sheet in this OBSERVATION & EQUATIONS: before heating the
solution such that about 1/2 of the sheet projects above solution was yellow. After heating, pale yellow precipitate
the surface of the solution. Allow it to stand for 15 to 20 formed Iodoform
minutes. Remove the sheet and test its solubility in hot CH3COCH3 +4NaOH + 3I2 -> CH3COONa + CHI3 + 3NaI
water. Observe the portion which did not come in contact + 3H2O
with the solution.

OBSERVATION: Portions of gelatin that got exposed to

formalin hardened While the portion that was not exposed EXPERIMENT 12
remain soft & turn into jelly PROPERTIES OF CARBOXYLIC ACID and SALICYLIC
ACID
4. Silver Mirror Test or Tollens’s Test:
|. PURPOSE: To learn physical properties of Carboxylic Acid
Place 2 mL of an ammoniacal solution of silver nitrate in and the different reactions of Salicylic Acid
each of 3 clean and dry test tubes. To one add 5 drops
formalin, to the second 5 drops of benzaldehyde and to ||. APPARATUS: Test tubes, droppers, breaker, mortar & pestle,
the third, 5 drops of acetone. Agitate the mixture in each Bunsen burner, Clay Shield, Wire gauze, funnel, filter paper
tube thoroughly then warm in the water bath. After the |||. MATERIALS: Acetic Acid, Benzoic Acid, Stearic Acid,
mirror has formed. throw out the contents of the tube and Formic Acid, Oxalic Acid, 0.5% Potassium permanganate,
rise with distilled water. water, Salicylic Acid, Ferric Chloride
|V. PROCEDURE: Ferric Nitrate, Bromine water, Million’s
OBSERVATION: Tube w/ formalin = Formation of Reagent, Soda lime, Methyl Alcohol, conc. Sulfuric Acid,
metallic Silver, Tube w/ benzaldehyde = White solution,
Yellowish upper, cloudy, Tube w/ Acetone no reaction 1. SOLUBILITY OF CARBOXYLIC ACID IN WATER:

EQUATION: Test the solubility in water of the following acids; acetic,

benzoic, and stearic acid. Use 3 drops of liquid (or a pinch if
H-CHO + 2Ag(NH3)2OH + H2O -> H-COOH + 2Ag + solid) to 3 mL of water. Account for the large observed
4NH3 + 2H2O differences in solubility between acetic acid and stearic acid

C6H5CH + 2Ag(NH3)2OH + H2O -> C6H6COOH + 2Ag + Why would stearic acid be expected to show a lower solubility
4NH3 +H2O in water? Has long hydrocarbon chain, is hydrophobic and
repels the water molecules to the extent that the compound is
(CH3)2CO + 2Ag (NH3)2OH -> NO REACTION insoluble in water.

5. Fehling's Test: 2. ACTION OF AN OXIDIZING AGENT ON THE

CARBONYL GROUP:
Place 1 mL of Fehling's Solution in each of 3 test tubes.
To one add a few drops of formalin, to the second, a few Place 5 drops of acetic, formic, benzoic and oxalic acid in four
drops of benzaldehyde and to the third, a few drops of separate test tubes and add 1 mL of 0.5% potassium
acetone. Mix the contents in each tube thoroughly and permanganate to each tube. Heat the four test tubes in a water
warm in a water bath. bath, and note if any reduction of the permanganate occurs.

OBSERVATION: Test tube w/ formalin blue color Write the equations involved.
solution turns brick red precipitate, Test tube w/ NR for Acetic and Benzoic Acid
benzaldehyde = remains blue, Test tube w/ Acetone = No HCOOH + KMNO + 6H +  6CO2 2H2O + 2Mn+ 2 +KOH
(COOH)2 + KMNO+ + 6H+  4H20 + 10CO2 + 2Mn+2 + KOH
reaction

EQUATION: 3. PREPARATION OF SALICYLIC ACID SOLUTION:

Add 15 mL of water to 0.1 gram of salicylic acid and shake the anhydride. Add 3 drops of concentrated sulfuric acid and attach
solution for a few minutes, filter the solution and divide the a long glass tubing with a cork (serves as an air condenser) and
filtrate into three portions, and use them as stated below: 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
a. Reaction with Ferric ions. by cooling the flask in an ice bath. When the crystallization is
complete, separate the aspirin crystals by filtration. Dry the
To the first five mL portion of the prepared solution, add 1 or 2 crystals by pressing between filter papers. When sufficiently
drops of ferric chloride or ferric nitrate solution. dry, get the weight of the aspirin crystals.

Observation: Purple reaction after adding FecI3 Write the equation for the synthesis:

Equation: C6H4OH COOH + 3Br2  ( C6H4OHCOO )3 + C7H6O3 + (CH3CO)2 O  Ca H8 O4 + CH3 COOH

3HBr + CO2
Weight of dry aspirin = 180. 157g/mol
b. Reaction with Bromine Water
Calculate:
To the second 5 mL portion of the prepared solution, add a few
drops of bromine water, a few drops at a time until a light a. the theoretical yield
yellow solution is obtained.
1mole Apirin 180.157 g Aspirin
0.0217 mole SA x x
OBSERVATION: 1 mole SA 1 mole Aspirin
= 3.9 g Aspirin
The solution initially became translucent white to a faint yellow
color.
b. the % yield
EQUATION: Br OH Actual Yield 3.0 g Aspirin
x 100 = x 100 = 76.9%
C6H4OHCOOH + 3Br2  +3HBr + CO2 Theoretical Yield 3.9 g Aspirin
Br Br
c. Reaction with Million’s reagent.

To the last five mL portion of the solution prepared solution, add

1 or 2 drops of Million’s reagent, and warm the mixture.
Observe the color of the precipitate.

Observation:

Precipitate at the bottom and light – red colored solution

Equation: C6H4OH COOH + Hg N2 O6  C6 H4 OH COOHg

+2NO2

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

Equation: C6 H4 OH COOH OH
+ CO2
NaOH H
5. ESTER FORMATION : CaO

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 )

Equation: CH3OH + C6 H4OHCOOH C6 H4 OH

COOCH3 + H20

EXPERIMENT 13
PREPARATION OF ASPIRIN H2SO4

|. 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