COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

Experiment No. 8

BENZAMIDE

I. Objectives
At the end of the experiment the student should be able to synthesize Benzamide and
determine its identity through chemical tests and FTIR.

II. Materials
Equipments/Apparatus
Beaker Casserole
Graduated cylinder Mettler balance
Hot plate Distillation set-up
Pipette Reflux set-up
Pycnometer separatory funnel
Test tubes Aspirator
Watch glass

Chemicals/Reagents
Bleaching powder Potassium bichromate
Sodium acetate Alcoholic silver nitrate

III. Procedure
A. Synthesis
1. Place 5 ml of concentrated ammonia solution in a 50 ml flask.
2. Cool in ice.
3. Add 1 ml of benzoyl chloride drop by drop. Shake the flask frequently.
4. Allow to stand for 10-15 minutes.
5. Filter off the precipitate.
6. Wash with a little cold water.
7. Collect the crystals and dry.
8. Calculate for percentage yield.

B. Chemical Tests
a. Hydrolysis using an alkali – Add 2 ml of 10% NaOH to 0.5 g of sample placed in
a test tube. Heat the mixture to boiling. Test the reaction of vapor produced using litmus
paper.
b. Acid hydrolysis - Add 2 ml of dilute hydrochloric acid to 0.5 g of sample placed in
a test tube. Test the reaction of vapor produced using litmus paper.
c. Action of nitrous acid – Add 2-3 ml of diluted hydrochloric acid to 0.5 gram
sample placed in a test tube. Then add 3 ml of 10% sodium nitrite solution. Note any
change.

C. FTIR

Subject the synthesized product to FTIR analysis.

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 COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

IV. Data Sheet

NAME: GROUP NO:

DATE: SCORE:

Experiment No ______
Experiment Title

Balanced reaction:

Experimental data

Reactants Molecular weight Density Amount used

Products Molecular weight Amount produced

Calculations:
Actual Yield ___________________
Theoretical Yield ___________________
Percentage Yield ___________________

Results
Identification Tests:
A. Physical Tests
1. Appearance ________________________
2. Odor _______________________
3. Boiling point ________________________
4. Specific gravity ________________________

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COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

B. Chemical Test
Hydrolysis using an alkali
Chemical reaction

Result: ________________________________________________

Acid hydrolysis
Chemical reaction

Result: ________________________________________________

Action of nitrous acid

Chemical reaction

Result: ________________________________________________

C. FTIR spectrum of Benzamide

(Cut the printed result and attached the IR spectrum in the area given below. Encircle and label
the peaks of the identified functional groups in Benzamide)

Remarks

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COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

Questions:

1. Write down and complete the following reactions to illustrate methods of

preparing amides:

a. ammonium acetate + heat

b. ethyl acetate + ammonium hydroxide

c. hydrolysis of propylnitrile

2. Name five examples of drug products classified as amides. Give their structure
and uses.

3. Illustrate the biotransformation pathways of amide drugs.

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 COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

NAME: GROUP NO:

DATE: SCORE:
Experiment No ______
Experiment Title

ASSESSMENT RUBRIC
Criteria Exemplary Proficient Good Needs Unacceptable Score/
Improvement Comments
(5) (4) (3) (2) (1)
Materials, All equipment All necessary supplies All necessary Some necessary Many necessary
Preparedness accurately placed on hand. supplies on hand. supplies must be supplies are
and Personal All necessary supplies Sound understanding Partial searched out. unavailable
Safety on hand of health and safety understanding of Serious deficiencies No understanding or
Very neat and issues. Student wears health and safety in addressing health appreciation of safety
organized. complete PPE most of issues. Student and safety issues. and health related
Complete the time. wears complete PPE Students’ PPE are issues. Student does
understanding of health occasionally. incomplete. not wear the PPE
and safety issues. required.
Student wears
complete PPE at all
times.
Procedure Demonstrates Demonstrates Experiment was Poor understanding Works in disorderly
understanding of the understanding of the performed with of the procedure manner right at the
procedure with no procedure with minimal minimal assistance. and was able to start. No output was
assistance needed. assistance needed. Received several perform experiment presented.
Works in a clean and Works in an organized reminders on with assistance.
organized manner but receives seldom observing
practicing safety reminder on observing cleanliness and
measures at all times. cleanliness and safety safety measures.
measures from the
instructor.
Product Correct product was Correct product was Product synthesized Was able to No product was
synthesized as synthesized as conformed to the synthesize but synthesized.
confirmed by confirmed by physical test and product was not
identification tests. identification tests. most of the chemical able to meet the
Actual yield meets the Actual yield does not tests specifications of
theoretical yield. meet the theoretical both physical and
yield. chemical tests.
Time Completeness of Complete most of the Complete most of Sometimes off task Does not complete any
Management assigned task on time. assigned task on time the assigned task of the assigned task on
but not on time time.
Computations Correct and accurate. Correct and accurate, Imprecise answer With correct formula Incorrect answer and
Organized, with with missing units or but with correct and appropriate unable to present any
formulas and symbols. Correct formula and units or symbols. solutions.
substitutions. formula and solutions. substitution, with Incorrect final
Complete, with correct units or answer.
appropriate symbols, symbols
units or significant
figures.
Sanitation and Consistently uses Consistently uses Proper clean-up Needs to be Proper clean-up
Clean-up proper clean-up proper clean-up procedures reminded more than procedures are seldom
procedures procedures generally used once during the lab used.
Often will help other Station generally neat May need some help to use proper clean- Often requires help to
students to complete and clean on occasion to up procedures complete clean-up
tasks properly complete tasks 1 or 2 items left at 3 or more items left at
Station always left neat Station generally left station or not station or station not
and clean clean cleaned cleaned
Documentation Organized, neat and Organized, neat and Neat but with some Illegible, All answers are
legibly written. legibly written. unreadable parts. organization is poor, incorrect or no answer
Answers completely Incorrect answer to one Incorrect answers to incorrect answers to at all.
and correctly with cited of the questions. 2 questions 3 or more questions.
references References were cited No references cited
TOTAL

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COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

Experiment No. 9

ACETAMINOPHEN

I. Objectives
At the end of the experiment the student should be able to synthesize Acetaminophen and
determine its identity through chemical tests and FTIR.

II. Materials
Equipments/Apparatus
Beakers Stirring rod
Clamp Vacuum filtration set-up
Dropper Ring stand
Graduated cylinders Watch glass
Melting point apparatus Erlenmeyer flask
Melting point capillary tube
Pipette

Chemicals/Reagents
p-aminophenol
Acetic anhydride
Phosphoric acid, concentrated
Ethanol

III. Procedure
A. Synthesis
1. Bring to boiling half the water content of a 400-ml capacity beaker.
2. Weigh out 1.5 g of p-aminophenol and transfer it into a 125-mL Erlenmeyer flask.
(Caution! Avoid contact with skin.)
3. Add 25 ml of water. Add 20 drops of concentrated phosphoric acid, and swirl the
flask until all of the amine dissolves. If not, add a few more drops of phosphoric
acid.
4. Turn off the hot plate. Place the flask in the hot water.
5. Carefully add 2 ml of acetic anhydride to the flask.
6. Leave the flask in the warm water for 10 minutes.
7. Remove the flask and place it an ice-water bath.
8. Stir the mixture to crystallize the Acetaminophen. (Scratching the walls of the
flask may be done to start the crystallization. If no crystals appear, add a small
seed of acetaminophen to start the crystal formation).
9. Allow the flask to stay in the ice-water bath for 30 minutes.
10. Collect the crystals in a Buchner funnel using vacuum filtration.
11. Wash the crystals with 10 mL of cold water.
12. Allow the crystals to dry and weigh
13. Calculate the percentage yield.

B. Identification tests
1. Perform Thin Layer Chromatography

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 COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

2. Perform FTIR
Subject the synthesized product to FTIR analysis.

V. Data Sheet

NAME: GROUP NO:

DATE: SCORE:

Experiment No ______
Experiment Title
Balanced reaction:

Experimental data

Reactants Molecular weight Density Amount used

Products Molecular weight Amount produced

Calculations:
Actual Yield ___________________
Theoretical Yield ___________________
Percentage Yield ___________________

Results
Identification Tests:
A. Physical Tests
1. Appearance ________________________
2. Odor ________________________
3. Melting point ________________________

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COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

C. FTIR spectrum of Acetaminophen

(Cut the printed result and attached the IR spectrum in the area given below. Encircle and label
the peaks of the identified functional groups in Acetaminophen)

Remarks

Questions:

1. Under what class of compound is acetaminophen classified?

2. Why was it considered as safe analgesic?

3. Discuss the biotransformation of acetaminophen.

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 COLLEGE OF PHARMACY PHARMACEUTICAL AND MEDICINAL ORGANIC CHEMISTRY LAB

NAME: GROUP NO:

DATE: SCORE:
Experiment No ______
Experiment Title

ASSESSMENT RUBRIC
Criteria Exemplary Proficient Good Needs Unacceptable Score/
Improvement Comments
(5) (4) (3) (2) (1)
Materials, All equipment All necessary supplies All necessary Some necessary Many necessary
Preparedness accurately placed on hand. supplies on hand. supplies must be supplies are
and Personal All necessary supplies Sound understanding Partial searched out. unavailable
Safety on hand of health and safety understanding of Serious deficiencies No understanding or
Very neat and issues. Student wears health and safety in addressing health appreciation of safety
organized. complete PPE most of issues. Student and safety issues. and health related
Complete the time. wears complete PPE Students’ PPE are issues. Student does
understanding of health occasionally. incomplete. not wear the PPE
and safety issues. required.
Student wears
complete PPE at all
times.
Procedure Demonstrates Demonstrates Experiment was Poor understanding Works in disorderly
understanding of the understanding of the performed with of the procedure manner right at the
procedure with no procedure with minimal minimal assistance. and was able to start. No output was
assistance needed. assistance needed. Received several perform experiment presented.
Works in a clean and Works in an organized reminders on with assistance.
organized manner but receives seldom observing
practicing safety reminder on observing cleanliness and
measures at all times. cleanliness and safety safety measures.
measures from the
instructor.
Product Correct product was Correct product was Product synthesized Was able to No product was
synthesized as synthesized as conformed to the synthesize but synthesized.
confirmed by confirmed by physical test and product was not
identification tests. identification tests. most of the chemical able to meet the
Actual yield meets the Actual yield does not tests specifications of
theoretical yield. meet the theoretical both physical and
yield. chemical tests.
Time Completeness of Complete most of the Complete most of Sometimes off task Does not complete any
Management assigned task on time. assigned task on time the assigned task of the assigned task on
but not on time time.
Computations Correct and accurate. Correct and accurate, Imprecise answer With correct formula Incorrect answer and
Organized, with with missing units or but with correct and appropriate unable to present any
formulas and symbols. Correct formula and units or symbols. solutions.
substitutions. formula and solutions. substitution, with Incorrect final
Complete, with correct units or answer.
appropriate symbols, symbols
units or significant
figures.
Sanitation and Consistently uses Consistently uses Proper clean-up Needs to be Proper clean-up
Clean-up proper clean-up proper clean-up procedures reminded more than procedures are seldom
procedures procedures generally used once during the lab used.
Often will help other Station generally neat May need some help to use proper clean- Often requires help to
students to complete and clean on occasion to up procedures complete clean-up
tasks properly complete tasks 1 or 2 items left at 3 or more items left at
Station always left neat Station generally left station or not station or station not
and clean clean cleaned cleaned
Documentation Organized, neat and Organized, neat and Neat but with some Illegible, All answers are
legibly written. legibly written. unreadable parts. organization is poor, incorrect or no answer
Answers completely Incorrect answer to one Incorrect answers to incorrect answers to at all.
and correctly with cited of the questions. 2 questions 3 or more questions.
references References were cited No references cited
TOTAL

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