Note: All the red inked data are experimental & it will vary according to the group

Experiment name: Preparation of Acetanilide (Acetic Acid Method)

Introduction
Acetanilide is an important organic compound used in the synthesis of pharmaceuticals and dyes. It is an amide
derived from aniline and acetic acid. The reaction involves the acetylation of aniline, where aniline acts as a
nucleophile and attacks the carbonyl carbon of acetic acid, leading to the formation of acetanilide and water as a
byproduct.
This experiment aims to synthesize acetanilide from aniline using glacial acetic acid as the acetylating agent. The
crude product is isolated, purified through recrystallization, and its purity is confirmed by determining its melting
point.
Chemical Reactions
The reaction between aniline and acetic acid proceeds as follows: (Use the aromatic one)

C6H5NH2+CH3COOH→C6H5NHCOCH3+H2O
Reaction Mechanism (যে পার া কর দিও এর া সময় নাই ক া
1. Nucleophilic attack: The lone pair on the nitrogen of aniline attacks the electrophilic carbonyl carbon of acetic
acid.
2. Formation of the intermediate: A tetrahedral intermediate forms, which is unstable.
3. Elimination of water: The intermediate collapses, eliminating water and forming acetanilide.
Materials and Methods
Reagents
• Aniline (5.0 mL) • Activated charcoal (0.5 g, approx. half a
teaspoon)
• Glacial acetic acid (8.0 mL)
• Distilled water (20 mL for recrystallization)
• 5% Aqueous NaOH solution (200 mL)
Apparatus
• 250 mL quick-fit conical flask • Thermometer
• Air condenser • Watch glass
• 100 mL beaker • Ice bath
• Suction filtration • Hot plate
Procedure
Synthesis of Acetanilide
1. Reaction Setup: In a 250 mL quick-fit conical flask, 5.0 mL of aniline and 8.0 mL of glacial acetic acid were
added.
2. Reflux: An air condenser was attached (without water circulation), and the mixture was heated under reflux at
104–106°C for 1.5 hours.
3. Completion of Reaction: The reaction was considered complete when temperature fluctuations were
observed due to water removal.
4. Precipitation of Crude Acetanilide: The reaction mixture was poured in a thin stream into 200 mL of 5%
aqueous NaOH while stirring. The solution was cooled in an ice bath, leading to the precipitation of white
crystalline acetanilide.
 5. Filtration & Drying: The crude acetanilide was collected by suction filtration, washed with cold water, and
dried for 4–5 minutes. It was then left to dry overnight.
Purification by Recrystallization
1. Dissolution: The crude acetanilide was dissolved in 20 mL of distilled water in a 100 mL beaker and heated
until a clear solution formed.
2. Decolorization: About 0.5 g of activated charcoal was added, and the mixture was boiled for 5 minutes to
remove impurities.
3. Filtration: The hot solution was filtered using suction filtration to remove the charcoal.
4. Crystallization: The filtrate was cooled to room temperature, resulting in the formation of purified acetanilide
crystals.
5. Final Collection & Drying: The purified acetanilide was collected by suction filtration and left to dry
overnight.
Melting Point Determination
The melting point of the purified acetanilide was determined using a melting point apparatus and compared to the
literature value of 169°C.
Results
Observations
Step Observations
Reaction Mixture Clear solution formed upon mixing aniline and acetic acid.
During Reflux No color change observed; temperature remained stable at 104–106°C.
After Addition to NaOH White crystalline solid formed.
Crude Product Appearance White crystals collected after filtration.
After Recrystallization More refined white crystals formed.

Experimental Data
1. Mass of crude acetanilide = 4.2 g
2. Mass of purified acetanilide = 3.5 g
3. Melting point of purified acetanilide = 169°C (matches literature value)
Yield Calculation
Molecular Weights:
• Aniline (C₆H₅NH₂), M= 93.13 g/mol
• Density of aniline, D = 1.02 g/mL
• Volume of aniline, V= 5mL
• Acetanilide (C₆H₅NHCOCH₃), M2 = 135.17 g/mol
Moles of Aniline Used:
𝑉 × 𝐷 5.0 𝑚𝐿 × 1.02 𝑔/𝑚𝐿
𝑀𝑜𝑙𝑒𝑠 𝑜𝑓 𝑎𝑛𝑖𝑙𝑖𝑛𝑒, 𝑤 = = = 0.0548 𝑚𝑜𝑙
𝑀 93.13 𝑔/𝑚𝑜𝑙
Theoretical Yield:
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 = 𝑤 × 𝑀2 = 0.0548 × 135.17 = 7.41 𝑔
Percentage Yield Calculation:
• Crude Acetanilide:
4.2
𝑃𝑒𝑟𝑐𝑒𝑛𝑡𝑎𝑔𝑒 𝑦𝑖𝑒𝑙𝑑 = × 100 = 56.6%
7.41
 • Purified Acetanilide:
3.5
𝑃𝑒𝑟𝑐𝑒𝑛𝑡𝑎𝑔𝑒 𝑦𝑖𝑒𝑙𝑑 = × 100 = 47.2%
7.41
Discussion
The experiment successfully synthesized acetanilide using aniline and glacial acetic acid. The crude acetanilide was
isolated using NaOH, which neutralized excess acetic acid and helped in precipitation. The purification step through
recrystallization significantly improved product purity, as confirmed by the melting point measurement (169°C),
which matched the literature value.
The percentage yield of crude acetanilide was 56.6%, while the yield after recrystallization was 47.2%. The loss in
yield was expected due to solubility losses and filtration steps during purification.
Some possible reasons for yield loss include:
• Incomplete crystallization due to improper cooling.
• Product retention in the filtration paper and glassware.
• Solubility loss during recrystallization.
Lab Safety Precautions
1. Personal Protective Equipment (PPE): A lab coat, safety goggles, and gloves were worn at all times.
2. Aniline Handling: Since aniline is toxic and can be absorbed through the skin, it was handled carefully, and
direct contact was avoided.
3. Glacial Acetic Acid: As a corrosive substance, it was handled carefully to prevent skin contact and inhalation.
4. Reflux Safety: The air condenser was securely attached, and the reaction mixture was refluxed at 104–106°C.
Water was not passed through the condenser jacket.
5. Sodium Hydroxide: The 5% NaOH solution was handled carefully, and any spills were rinsed with plenty of
water.
6. Filtration & Recrystallization: Precautions were taken to avoid burns during hot filtration, and activated
charcoal was handled carefully to prevent airborne dispersion.
7. General Safety: Flammable substances were kept away from heat, chemical waste was disposed of properly,
and any accidents were reported immediately.
Conclusion
The experiment demonstrated the successful synthesis and purification of acetanilide using the acetic acid method.
The product was obtained in moderate yield and confirmed to be pure through melting point analysis. The principles
of reflux, precipitation, filtration, and recrystallization were effectively applied in this experiment.

Experiment name: Preparation of p-Nitro acetanilide

Introduction:
Acetanilide (C₈H₉NO) is an aromatic amide compound that can undergo electrophilic substitution reactions, such as
nitration, to introduce nitro groups into its structure. The goal of this experiment is to synthesize p-nitro acetanilide, a
compound where a nitro group is introduced at the para position of the benzene ring, using a mixture of concentrated
sulfuric acid and nitric acid. The product will then be purified by recrystallization, and its yield and melting point will
be determined to assess the purity.

Reaction Mechanism
Reaction Equation:
 H2SO4
C8H9NO+HNO3 → C8H8N2O3+H2O
Mechanism of Nitration:
1. Generation of the Nitronium Ion (NO₂⁺):
o The nitrating mixture (HNO₃ + H₂SO₄) generates the highly electrophilic NO₂⁺ ion.

Electrophilic Aromatic Substitution & Restoration of Aromaticity:

o The nitronium ion (𝑵𝑶₂⁺) attacks the para-position of acetanilide due to the electron-donating effect
of the acetamide (-NHCOCH₃) group, forming a resonance-stabilized arenium ion.
o A proton (H⁺) is lost, and the aromaticity of the benzene ring is restored, forming p-nitro acetanilide as
the major product.

Materials & Chemicals

• Acetanilide (8.0 g) • Concentrated nitric acid (HNO₃) (4.0 mL)
• Glacial acetic acid (8-9 mL) • Crushed ice
• Concentrated sulfuric acid (H₂SO₄) (15 mL) • Rectified spirit (for recrystallization)
Apparatus
• 250 mL conical flask • Water condenser
• 100 mL conical flask / beaker • Glass rod
• Suction filtration • Ice bath
• Watch glass • Oven
Procedure
1. Nitration Reaction:
1. Dissolution of Acetanilide:
o 8.0 g of purified acetanilide was placed in a 250 mL conical flask.
o 8-9 mL of glacial acetic acid and 15 mL of concentrated sulfuric acid were added to dissolve it
completely.
o The mixture was cooled using an ice bath.
2. Preparation of Nitrating Mixture:
o 4.0 mL each of concentrated nitric acid and concentrated sulfuric acid were mixed in a separate small
beaker and cooled in an ice bath.
3. Addition of Nitrating Mixture:
o The cold nitrating mixture was slowly added dropwise to the cooled solution of acetanilide with
continuous stirring.
o The temperature was carefully maintained below 10°C.
o After complete addition, the reaction mixture was removed from the ice bath and left to stand for one
hour.
4. Isolation of Crude Product:
o The reaction mixture was poured into 200 mL of cold water containing crushed ice.
o Crude p-nitro acetanilide precipitated out.
 o The solid was collected by suction filtration, washed with cold distilled water, and dried in an oven at
100°C.

Purification by Recrystallization
1. Dissolution in Rectified Spirit:
o The crude product was dissolved in minimum rectified spirit in a 100 mL conical flask.
o The solution was heated under reflux with a water condenser until a clear solution was obtained.
2. Crystallization:
o The flask was removed from heat and allowed to cool to room temperature, where pale-yellow
crystals of p-nitroacetanilide separated out.
3. Collection and Drying:
o The purified crystals were collected by suction filtration, transferred to a watch glass, and dried
overnight.
4. Melting Point Determination:
o The melting point of dried p-nitroacetanilide was recorded and compared to the authentic value (214–
216°C).

Observations & Results

Parameter Crude Product Purified Product

Appearance Yellow solid Pale-yellow crystals

Mass (g) Measured value Measured value

Melting Point (°C) Measured value Measured value

Expected Melting Point (°C) – 214–216°C

Yield (%) Calculated Calculated

Experimental Data
1. Mass of pure p-Nitro acetanilide = x g
Calculations
1. Theoretical Yield Calculation
Balanced Equation:
C8H9NO+HNO3→C8H8N2O3+H2O
• Molar Mass of Acetanilide (C₈H₉NO) / Molecular weight of stating material: 135.16 g/mol
• Molar Mass of p-Nitroacetanilide (C₈H₈N₂O₃) / Molecular weight of ending material: 180.16 g/mol
• Mass of sample of acetanilide: 8g
180.16
Theoretical yield = × 8 = 10.66 𝑔
135.16
2. Percentage Yield Calculation
𝐴𝑐𝑡𝑢𝑎𝑙 𝑌𝑖𝑒𝑙𝑑
𝑃𝑒𝑟𝑐𝑒𝑛𝑡𝑎𝑔𝑒 𝑌𝑖𝑒𝑙𝑑 = ( ) × 100%
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑌𝑖𝑒𝑙𝑑

𝑥
= × 100%
10.66
Discussion
• The nitration of acetanilide proceeded via electrophilic substitution, favoring the para position due to the
directing effect of the amide (-NHCOCH₃) group.
• The yellow color of crude product indicated p-nitro substitution.
• Recrystallization in rectified spirit significantly improved purity, as observed in the melting point comparison.
• The yield and melting point were analyzed to determine reaction efficiency and purity.
Lab Safety Precautions
• Personal Protection: Gloves, goggles, and a lab coat were worn at all times.
• Handling Acids: H₂SO₄ and HNO₃ are highly corrosive—they were added slowly with proper ventilation.
• Temperature Control: The reaction temperature was kept below 10°C to prevent side reactions.
• Waste Disposal: Acidic waste was neutralized before disposal according to lab safety protocols.
Conclusion
The experiment successfully synthesized p-nitroacetanilide via electrophilic nitration of acetanilide. The purified
product exhibited a melting point close to the literature value (214–216°C), confirming its identity. The percentage
yield was calculated to assess efficiency.

Thank You