Princess Shyne C.

Davis BS BIOMED 1A 04/16/2024

FLOWCHART OF EXPERIMENT 9
CARBOXYLIC ACIDS AND DERIVATIVES
ACIDITY OF CARBOXYLIC ACIDS

Determine the pH of 0.1M acetic acid, monochloroacetic acid, trichloroacetic acid

ESTERIFICATION

Maintain the Place 3mL of the

Prepare a hot water
temperature at 60- alcohol in the dry
bath
70℃ test tube

Slowly add 10 drops

Dissolve 0.5g of
Place the test tube in of concentrated
solid or 1mL of liquid
water bath sulfuric acid with
acid with stirring
stirring

After 10 mins, if the Increase the

Allow it ti remain for odor of either acid or temperature another
at least 10 mins alcohol is still 10 degrees for 5
obvious mins

When there is
Take note of the reaction, pour the
odor contents of the tube
into 20mL of hot
water contained on a
CARBOXYLIC ACID AND ITS SALTS small beaker

Add a small amount of

salicylic acid to a test Add 5 mL of cold
Stir the mixture well.
tube. water to the test tube.

IF NOT
Carefully heat the DISSOLV
Does it dissolve?
] E
mixture until boiling.

IF IT
DISSOLV
E
Add 3M NaOH drop-
by-drop, swirling the
] Pour the solution into a
Cool the solution to
]
flask after each 50 mL Erlenmeyer
room temperature.
addition. flask.

Add 3M HCl to the

solution, drop-by-drop,
swirling after each Record observations
addition.

HYDROLYSIS OF ACID CHLORIDES

Add 2 drops of acetyl

Add 2 mL of water to chloride to one test tube
shake
each test tube. and 2 drops of acetic
anhydride to the other.

] Observe
Test the resulting Test the resulting
] (Acetyl chloride: More reactive,
exothermic reaction expected.
solutions with litmus solutions with litmus Acetic anhydride: Slower reaction
expected.)

• (Acetyl chloride: White precipitate

of silver chloride expected
Add 1 drop of aqueous (indicating the presence of
silver nitrate solution •
chloride ions).
Acetic anhydride: No precipitate
to each tube expected (acetic anhydride does
not contain chloride ions).

REACTIONS OF ESTERS (Acid Hydrolysis of Acetyl Salicylic Acid)

Place 0.5 g of Add 10 mL of water

Boil the mixture gently
acetylsalicylic acid and 1 drop of HCl to
for 3-5 minutes.
(aspirin) in a test tube. the test tube.

] Add 1-2 drops of ferric

] Filter the mixture to
Observe chloride solution to remove any
the cold filtrate. undissolved crystals.
REACTIONS OF AMIDES (Hydrolysis)

Add 2 mL of 10%
Add 0.5 g of the amide Basic Hydrolysis NaOH solution to the
to a test tube.
test tube.

]
Test for ammonia Heat the mixture to
Acid Hydrolysis
vapor boiling.

Mix 2 mL of diluted
hydrochloric acid with 0.5 Heat the mixture to
g of amide or residue boiling. Compare Results
from basic hydrolysis in a
test tube.

Record all observations from both tests, including:

1. Presence or absence of ammonia evolution.
2. Any physical changes in the reaction mixtures (color change, precipitate
formation, etc.).
Princess Shyne C. Davis BS BIOMED 1A 04/16/2024

EXPERIMENT 9
CARBOXYLIC ACIDS AND DERIVATIVES
PRELABORATORY ASSIGNMENT
1. SDS:
a. Acetic Acid:
i. Hazards: Flammable liquid, corrosive to skin and eyes, strong
odor.
ii. Safety: Wear gloves, eye protection, and work in a well-ventilated
area. Avoid contact with skin and eyes.
b. Trichloroacetic Acid:
i. Hazards: Highly corrosive, toxic by inhalation, ingestion, and skin
contact. Severe irritant to skin, eyes, and respiratory system. Can
cause burns.
ii. Safety: Wear chemical resistant gloves, safety goggles or face
shield, and protective clothing. Use a fume hood.
c. Methyl Salicylate (Oil of Wintergreen):
i. Hazards: Flammable liquid, moderate skin and eye irritant. Can
be toxic in high doses.
ii. Safety: Wear gloves, eye protection, and work in a well-ventilated
area. Avoid contact with skin and eyes. Do not ingest.
d. Acetyl Chloride:
i. Hazards: Highly reactive, corrosive to skin and eyes, fumes are
very irritating to the respiratory system. Can react violently with
water.
ii. Safety: Wear chemical resistant gloves, safety goggles or face
shield, and a fume hood. Handle with extreme caution.
e. Aniline:
i. Hazards: Toxic by inhalation, ingestion, and skin contact. Readily
absorbed through skin. Carcinogen.
ii. Safety: Wear chemical resistant gloves, safety goggles or face
shield, and a respirator. Handle in a fume hood. Avoid contact
with skin and clothing.

2. Draw the structure:

Acetic acid Monochloroacetic acid Trichloroacetic acid Salicylic acid

Methyl salicylate Acetyl chloride Acetic anhydride aniline

salicylate
 urea acetamide benzamide

3. What is the effect of Cl on the acidity of carboxylic acids like monochloroacetic

acid and trichloroacetic acid?
a. Chlorine (Cl) increases the acidity of carboxylic acids like
monochloroacetic and trichloroacetic acid.
4. Write the equation that shows the ionization of valeric acid in water. Write
equations showing the reactions of valeric acid with NaOH.
a. Ionization:
CH₃CH₂CH₂CH₂COOH (aq) + H₂O (ℓ) ⇌ CH₃CH₂CH₂CH₂COO⁻ (aq) + H₃O⁺
(aq)
b. Reaction with NaOH (limited):
CH₃CH₂CH₂CH₂COOH (aq) + NaOH (aq) → CH₃CH₂CH₂CH₂COONa (aq) +
H₂O (ℓ)

5. Write the equation showing the ester formation.

a. RCOOH (aq) + R'OH (aq) ⇌ RCOOR' (aq) + H₂O (ℓ)
6. What is the purpose of adding ferric chloride to the filtrate of acetyl salicylic
acid?
a. The purpose of adding ferric chloride (FeCl₃) to the filtrate of acetyl
salicylic acid (aspirin) is to test for the presence of free salicylic acid.
7. How would you test for the ammonia vapor?
a. Smell: Ammonia has a strong, pungent odor. However, this method
should be used with caution as ammonia can irritate the respiratory
system. Only sniff cautiously if you suspect low concentrations and
have proper ventilation.
b. pH paper: Ammonia vapor reacts with moisture in the air to form
ammonium hydroxide (NH₄OH), a weak base. Holding a moistened
piece of litmus paper near the suspected ammonia source can show a
color change:
i. Red litmus paper turning blue: Indicates the presence of
ammonia vapor .