113L

CHEMISTRY LAB
MIDTERMS

PURPOSE
ACTIVITY 5
1. Formulation Development
● Properly formulate drugs and maximize
intended effects by incorporating excipients
COMPOUND IDENTIFICATION OF UNKNOWN
2. Drug Delivery Systems
DRUG SAMPLES USING PHYSICAL PROPERTIES ● Desired drug release profiles
3. Bioavailability
PHYSICAL PROPERTIES ● Solubility and absorption

1. QUALITY ASSURANCE
MELTING POINT RANGE
● Detection of physical changes
○ Presence of all contaminants and “The temperature from the point at which solid first
instability are a sign of poor quality begins to liquify to the point at which the entire sample
2. STABILITY ASSESSMENT is liquid.”
● Monitor and assess stability
○ Emulsion (separation of oil and water)
is a detection of instability
3. EARLY DETECTION OF CONTAMINATION
● Reveal the presence of
contaminants/impurities
The formation or presence of molds
○
and/or precipitations is an early
detection of contamination
4. BATCH TO BATCH CONSISTENCY
● Same quality within batches
○ Batch no. - series of numbers
○ Lot no. - portion of the batch

SOLUBILITY
PRINCIPLE
PRINCIPLE 1. Eutectic Point (Solid to Liquid)
● Like dissolves like meaning polar solutes dissolve ● Lowest temperature where phase
in polar solvents transformation is observed
● Solubility product (Ksp) 2. Phase Transition (Solid to Liquid)
○ Solubility product constant ● Very narrow temperature range
○ indication to determine if a sample is
contaminated but it should not be the Kinetic Energy and IMFA
sole basis to determine it ● Inversely proportional (Increased KE,
○ Ksp values are found in decreased IMFA)
pharmacopeias Triple Point
○ Sx = 2.00 –> Ksp = 1.6 ● Where solid, liquid and gas will exist
■ It means that Sx is simultaneously
contaminated because it does Critical Point
not match the one in the ● Difficult for liquid to be converted into gas state
pharmacopeia Supercritical Fluid
● What is reflected in the USP are pure ● Impossible to convert liquid into its gas state
substances (High pressure)

UY, CHARDONNAY 1
MIDTERMS

Carbon dioxide exists as a gas but if you reduce its MATERIALS

temperature and increase the pressure, this will 1. Capillary tube
allow them to associate. 2. Watch glass
3. Bunsen burner
4. Thermometer
PURPOSE
5. Rubber bands
1. Identification
2. Purity Assessment
3. Quality Control ACTIVITY 6

PHYSICAL PROPERTIES
● Can be determined/measured without DETECTION OF COMMON ELEMENTS
changing the composition or identity of the IN ORGANIC COMPOUNDS
substance
● Include color, odor, taste, density, melting, TEST FOR CARBON, HYDROGEN AND OXYGEN
boiling, conductivity and hardness
COMBUSTION REACTION | REDOX
CHEMICAL PROPERTIES
- A chemical reaction in which there is a transfer
● How the substance interacts with other
of electrons between 2 substances
substances and may include reactions with
oxygen (oxidation), chlorine, metals etc.
𝐶12𝐻22𝑂11 + 𝐶𝑢𝑂 → 𝐶𝑂2 + 𝐶𝑢
𝐶𝑂2 + 𝐶𝑎(𝑂𝐻)2 → 𝐶𝑎𝐶𝑂3 + 𝐻2𝑂
INTENSIVE PROPERTIES
● Independent of the amount of substance being
examined 1 oxidized, 1 reduced
1. Solubility OIL RIG
2. Melting Point ● oxidation is losing, reduction is gaining
3. Boiling Point GEROA
4. Density ● gaining of electron is oxidation due to
reducing agent
DRUG SAMPLES LEROA
● losing of electron is reduction due to
1. Paracetamol (C8H9NO2)
oxidizing agent
2. Aspirin (C9H8O4)
3. Caffeine (C8H10N4O2)
4. Salicylic acid (HOC6H4COOH) TEST FOR NITROGEN
5. Ascorbic acid (C6H8O6) DECOMPOSITION
6. Methylparaben (C8H8O3) - Single compound breaks down into 2 or more
7. Guaifenesin (C10H14O4) simpler substances
8. Chlorpheniramine maleate
9. Propylparaben (C10H12O3) 𝑁𝐻2𝐶𝑂 → 2𝑁𝐻3 + 𝐶𝑂2
10. Sulfamerazine (C11H12N4O2S)
𝑁𝐻3 + 𝑁𝑎𝑂𝐻 → 𝑁𝑎2𝐶𝑂3 + 𝐻2𝑂
11. Antipyrine (C11H12N2O)
12. Simethicone (C6H18O4Si3) 𝐶𝑂2 + 𝐶𝑎𝑂 → 𝐶𝑎𝐶𝑂3
Soda lime - Sodium hydroxide and Calcium oxide
SOLVENTS TEST FOR HALOGEN
1. Distilled water (H2O) 3. 1. BEILSTEIN TEST
2. Hexane (C6H14) SUBSTITUTION REACTION | REDOX
3. Ethanol (C2H5OH) - One or more atoms/groups in a
4. Glycerol (C3H8O3) molecule are replaced by another
atom, ion or group

UY, CHARDONNAY 2
MIDTERMS

𝐶𝐻𝐶𝑙3 + 𝐶𝑢𝑂 → 𝐶𝑢𝐶𝑙2 + 𝐻2𝑂 SOLUBILITY

𝐶𝐻𝐶𝑙3 + 𝐶𝑎𝑂 + 𝑁𝑎𝑂𝐻 → 𝐶𝑎(𝑂𝐻)2 + 𝑁𝑎𝐶𝑙 + 𝑁𝑎2𝐶𝑂3 PRINCIPLE
𝑁𝑎2𝐶𝑂3 + 𝐻𝑁𝑂3 → 𝑁𝑎𝑁𝑂3 + 𝐶𝑂2 Like dissolves like
● Polar solvents like water tend to dissolve polar
drugs
3. 2. SILVER NITRATE TEST
● Polar compounds have electrical charges
PRECIPITATION | DEHALOGENATION
Solubility Product (Ksp)
- Removal of a halogen atom from a
● If the concentration of the solute exceeds the
compound
Ksp, the solution becomes supersaturated and
may form a precipitate
COMPLEXATION | COORDINATION REACTION
- Involves the formation of complex ions
PURPOSE
by the interaction of metal ions with
Quality Control
ligands
● Solubility tests
○ Any significant changes in solubility
𝐴𝑔𝐶𝑙 + 𝑁𝐻3 → [𝐴𝑔(𝑁𝐻3)2] 𝐶𝑙
may indicate degradation/formulation
𝐴𝑔𝐶𝑙 + 𝑁𝐻3 → 𝐴𝑔𝐶𝑙 + 𝑁𝐻3
issues

3. 2. CONFIRMATORY TEST MELTING POINT RANGE

Complex
PURPOSE
- Can undergo reversible changes
Purity Assessment
- Association of 2 compounds; maintains
● Broader – impurities
individual properties
● Narrower – purer substance
- Gets destroyed = liberate reactant

Quality Control
A. Aspirin (Acetylsalicylic Acid)
TEST FOR SULFUR & PHOSPHORUS
- ≈138-140°C
1. OXIDATION - Deviations
- Loss of electrons by a chemical species - Other salicylate compounds
leading to an increase in its oxidation - Once exposed to a particular
state. temperature, it will have its own temp
which it will be converted to its liquid
𝐶76𝐻120𝑁20𝑂23𝑆6 (𝐸𝑔𝑔 𝑎𝑙𝑏𝑢𝑚𝑖𝑛) + 𝐾𝑁𝑂3 + 𝑁𝑎2𝐶𝑂3 → state
𝐾2𝐻𝑃𝑂4 + 𝐾2𝑆𝑂4 + 𝐾𝑁𝑂2 + 𝑁𝑎2𝑂 + 𝐶𝑂2 + 𝑁2 B. Paracetamol (Acetaminophen)
𝐾2𝑆𝑂4 + 2𝐻𝑁𝑂3 → 𝐾𝑁𝑂3 + 𝐻2𝑆𝑂4 - ≈168-172°C
- Variations
𝐻2𝑆𝑂4 + 𝐵𝑎𝐶𝑙2 → 𝐵𝑎𝑆𝑂4 + 2𝐻𝐶𝑙
C. Ibuprofen
- ≈75-78°C
2. COLORIMETRY
- Determination of its MP
- Formation of a complex that reflects
the presence of a particular compound
2 Types of Ingredients
1. Pharmaceutic Ingredient (Inactive ingredient)
𝐶76𝐻120𝑁20𝑂23𝑆6 (𝐸𝑔𝑔 𝑎𝑙𝑏𝑢𝑚𝑖𝑛) + 𝐾𝑁𝑂3 + 𝑁𝑎2𝐶𝑂3 →
2. Pharmacologic Ingredient (Active ingredient)
𝐾2𝐻𝑃𝑂4 + 𝐾2𝑆𝑂4 + 𝐾𝑁𝑂2 + 𝑁𝑎2𝑂 + 𝐶𝑂2 + 𝑁2
𝐾2𝑃𝑂4 + (𝑁𝐻4)6𝑀𝑜7𝑂24 + 𝐻𝑁𝑂3 → DEFINITION OF TERMS
(𝑁𝐻4)3𝑃𝑂4𝑀𝑜𝑂3 + 𝑁𝐻4𝑁𝑂3 + 𝐻2𝑂 Diluent
- Pharmaceutic ingredient that increases or
PHYSICAL PROPERTIES gives bulk in the formulation for the
convenience of patients to use
1. QUALITY ASSURANCE
● Organoleptic evaluation

UY, CHARDONNAY 3
MIDTERMS

Caplet 9. Egg Albumin (C6H8N2O4)

- Tablet shaped like a capsule 10. Potassium Nitrate (KNO3)
Liberation 11. Sodium Carbonate (NaCO3)
- Get released in the dosage form 12. Barium Chloride (BaCl2)
Liver 13. Ammonium Molybdate ((NH4)6Mo7O24)
- Major organ for metabolism 14. Distilled water (H2O)
Kidneys 15. Silver Nitrate solution (AgNO3)
- Major organ for excretion 16. Dilute Ammonia Solution (NH3)
A - Absorption 17. Concentrated Ammonia Solution
D - Distribution
M - Metabolism DRUG SAMPLES
E - Excretion 1. Mefenamic Acid (C15H15NO2)
Insulin 2. Chlorpheniramine maleate
- Best absorbed in the fatty tissue 3. Calcium phosphate (Ca3(PO4)2)
4. Paracetamol (C8H9NO2)
5. Povidone-iodine (C6H9I2NO)

MATERIALS
1. Bent glass tube with stopper
2. Copper wire
3. Iron clamp

MELTING POINTS
1. Paracetamol - 169°C
Isoniazid 2. Ascorbic acid - 190°C
- Meds for primary complex 3. Acetylsalicylic acid (Aspirin) - 136°C
- For tuberculosis (lungs) 4. Maalox - 360°C
5. Thiamine - 250°C
↑ temperature, solid – liquid 6. Nicotinamide - 128°C
↑ further temp, gas

ACTIVITY 7
Eutexia
- Phenomenon when 2 solids combined liquify
- Exploited by the pharmacy
ALKANES, ALKENES & ALKYNES

Score
- Manufacturer guarantees that whatever is INTRODUCTION TO HYDROCARBONS
present in the half is also present in the other ● Composed only of C and H
half ● Structural feature = presence of stable C-C
- No score, no guarantee bonds
● 4 general types
REAGENTS ○ Alkanes [C-C]
1. Sucrose (C12H22O11) ■ Saturated
2. Cupric Oxide (CuO) ■ Bound by single bond of
3. Lime Water (Ca(OH)2 + H2O) carbons
4. Soda Lime (CaHNaO2) ○ Alkenes [C=C]
5. Urea (CH4N2O) ■ Bound by double bonds
6. Chloroform (CHCl3) ■ Unsaturated
7. Carbon Tetrachloride (CCl4) ○ Alkynes [C≡C]
8. Dilute Nitric Acid (HNO3) ■ Bound by triple bonds

UY, CHARDONNAY 4
MIDTERMS

Aromatic hydrocarbons
○
Solubility Immiscible Immiscible Miscible in
■ Ring/Planar ring
in polar in polar non-polar,
● Simplest organic compound
slight
Miscible in Miscible in solubility in
non-polar non-polar polar
solvents
and are
insoluble in
water

ALKANES
CHEMICAL REACTIONS
● Relatively unreactive
● Acids, bases and strong oxidizing agent

A.1. REACTION WITH BROMINE

● Cyclohexane + Bromine /
SIMILARITIES ● Cyclohexane + bromine + Sunlight
● Physical properties
● Relatively non-polar (completely insoluble in
𝐶6𝐻14 + 𝐵𝑟2 𝐶6𝐻14 + 𝐵𝑟2 + Sunlight
water)
● Melting point and boiling point are determined
No reaction
by London dispersion forces
○ HC tend to become less volatile with
increasing molar mass

DIFFERENCES
● Chemical behaviors

PROPERTIES Sunlight - catalyst; may increase reactivity

A.2. REACTION WITH DILUTE 𝐾𝑀𝑛𝑂4

Physical Alkane Alkene Alkyne
● Cyclohexane + Dilute 𝐾𝑀𝑂4
Properties (Saturated (Olefins)
HC) ● No reaction

Color Colorless Colorless Colorless

Odor Odorless Distinctive Odorless

aroma (except
ethylene)
A.3. IGNITION
State Gas Gas Gas COMPLETE COMBUSTION
Solid Solid Solid - Cyclohexane ignited
Liquid Liquid Liquid - Clean flame
(depends (depends (depends 𝐶6𝐻12 + 9𝑂2 → 6𝐶𝑂2 + 𝐻2𝑂
on # of C on # of C on # of C Hexane
atom) atom) atom) 2𝐶6𝐻14 + 19𝑂2 → 12𝐶𝑂2 + 14𝐻2𝑂

Taste Waxy taste Distinct Slightly

taste acidic

UY, CHARDONNAY 5
MIDTERMS

ALKENES
CHEMICAL REACTIONS

B.1. REACTION WITH BROMINE

ADDITION REACTION
● Cyclohexene + 𝐵𝑟2
● Colorless Solution/ Colorless Product

C.4. BAEYER’S TEST FOR UNSATURATION

OXIDATION OF UNSATURATED MOLECULES
B.2. REACTION WITH DILUTE 𝐾𝑀𝑛𝑂4
● 𝐶2𝐻2 + Dilute 𝐾𝑀𝑂4
REDOX REACTION
● Violet color of 𝐾𝑀𝑂4 disappears, brown
● Cyclohexane + Dilute 𝐾𝑀𝑂4
sludge
● Colorless Solution/Product
● cis-1,2-cyclohenanediol
3𝐶6𝐻12 + 2𝐾𝑀𝑛𝑂4 + 4𝐻2𝑂 → 3𝐶6𝐻14𝑂2 + 2𝑀𝑛𝑂2 + 2𝐾𝑂𝐻

B.3. IGNITION C.5. FLAMMABILITY

INCOMPLETE COMBUSTION THEORETICAL COMPLETE COMBUSTION
● Cyclohexene ignited ● Acetylene ignited
● Yellow sooty flame 2𝐶2𝐻2 + 5𝑂2 → 4𝐶𝑂2 + 2𝐻2𝑂
𝐶6𝐻10 + 4𝑂2 → 3𝐶𝑂 + 3𝐶 + ↓ 5𝐻2𝑂 (𝑠𝑜𝑜𝑡)

C.6. FORMATION OF ACETYLIDES

ALKYNES DOUBLE DISPLACEMENT
CHEMICAL REACTIONS ● 𝐶2𝐻2 + Ammoniacal Cuprous Chloride
(𝐶𝑢𝐶𝑙 + 𝑁𝐻3)
C.1. PREPARATION OF ACETYLENE (ETHYNE,
● Red precipitate
NARCYLEN, VINYLENE)
𝐶2𝐻2 + 2𝐶𝑢𝐶𝑙 + 2𝑁𝐻3 → 𝐶𝑢2𝐶2 + 2𝑁𝐻4𝐶𝑙
DOUBLE DISPLACEMENT REACTION
● H−C≡C−H
C.7. REACTION WITH AMMONIACAL SILVER
● Calcium Carbide + Water
NITRATE/TOLLEN’S TEST
𝐶𝑎𝐶2 + 2𝐻2𝑂 → 𝐶𝑎(𝑂𝐻)2 + 𝐶2𝐻2 (𝑎𝑐𝑒𝑡𝑦𝑙𝑒𝑛𝑒 𝑔𝑎𝑠)
DOUBLE DISPLACEMENT
● 𝐶2𝐻2 + Ammoniacal Silver Nitrate
C.2. PHYSICAL PROPERTIES OF ACETYLENE
Solution (𝐴𝑔𝑁𝑂3 + 𝑁𝐻4𝑂𝐻)
● Colorless
● Faint garlic-like odor ● White precipitate
● Sweet taste
● Gas 𝐶2𝐻2 + 2𝐴𝑔𝑁𝑂3 + 2𝑁𝐻4𝑂𝐻 → 𝐶2𝐴𝑔2 + 2𝑁𝐻4𝑁𝑂3 + 2𝐻2𝑂

C.3. REACTION WITH BROMINE

ADDITION/HALOGENATION REACTION
● Acetylene gas (𝐶2𝐻2) + 𝐵𝑟2
● Colorless Solution/Product

UY, CHARDONNAY 6
MIDTERMS

ACTIVITY 8

SYNTHESIS & PROPERTIES OF ALCOHOL

PRE-LABORATORY REQUIREMENT
FERMENTATION
● process of central metabolism in which an
organism converts a carbohydrate, such as
starch or sugar, into an alcohol or an acid.
● Louis Pasteur - first scientist to study
fermentation
● Fermentation processes to produce wines,
beers and ciders are traditionally carried out
with Saccharomyces cerevisiae strains, the C.2. ETHYL ACETATE
most common and commercially available ● Ethanol + Glacial Acetic Acid + 𝐻2𝑆𝑂4
yeast then warmed + Alkalinized 𝑁𝑎2𝐶𝑂3
● Many other important industrial products are solution
the result of fermentation, such as yogurt, ● Plastic balloon like odor
cheese, bread, coffee
YEASTS 𝐶𝐻3𝐶𝑂𝑂𝐻 + 𝐶2𝐻5𝑂𝐻 ↔ 𝐶𝐻3𝐶𝑂𝑂𝐶2𝐻5 + 𝐻2𝑂
- Characterized by their capacity to ferment a
high spectrum of sugars, among which
D.1. DIFFERENTIATION OF ALCOHOL: LUCAS’ TEST
glucose, fructose, sucrose, maltose and
● a chemical test used to distinguish
maltotriose predominate, found both in ripe
between primary, secondary, and
fruit and in processed cereals
tertiary alcohols
DISODIUM PHOSPHATE
● Ethanol/Isopropyl/Tert-butyl Alcohol +
● As a neutralizing agent
Lucas Reagent then warmed and
● It acts as a buffering solution that helps control
shaken
pH
● Left to stand for 5 minutes

TEST FOR ETHYL ALCOHOL Lucas Reagent

C.1. IODOFORM TEST ● Anhydrous Zinc chloride (ZnCl2) +
● used to check the presence alcohols Concentrated Hydrochloric acid (HCl)
with the structure R-CH(OH)-CH3 in a
given unknown substance
Immediately After Types of
● Ethanol + Iodine + NaOH (warmed for 5
Upon standing for Alcohol
minutes)
Standing 5 mins
● Yellow precipitate (𝐶𝐻𝑙3)
(Triiodomethane precipitate) Distillate: Clear Clear Primary
Ethanol

Isopropyl Clear Cloudy Secondary

Alcohol Form 2 Solution
layers

Tert-Buty Cloudy Cloudy Tertiary

l Alcohol Solution Solution
Forms 2 2 layers
layers

UY, CHARDONNAY 7
MIDTERMS

ALCOHOLS (R-OH) CLASSIFICATIONS OF ALCOHOL

● Hydrocarbon derivatives in which one or more
hydrogens of a parent hydrocarbon have been
replaced by a hydroxyl or alcohol group
○ R – represents any alkyl group (methyl,
ethyl, propyl, and so on…)
REACTION
𝑅 − 𝑂𝐻 + 𝐻𝐶𝑙 → 𝑅𝐶𝑙 + 𝐻2𝑂
in the presence of 𝑍𝑛𝐶𝑙2 (catalyst)

CLASSIFICATIONS OF ALCOHOL

Immediately After Types of

Upon standing for Alcohol
Standing 5 mins

CLASSIFICATIONS OF ALCOHOL
Distillate: Clear Clear Primary
PRIMARY Ethanol

Isopropyl Clear Cloudy Secondary

Alcohol Solution

Tert-Buty Cloudy Cloudy Tertiary

l Alcohol Solution Solution

CLASSIFICATIONS OF ALCOHOL
SECONDARY

CLASSIFICATIONS OF ALCOHOL
TERTIARY

UY, CHARDONNAY 8