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Acetanilide Synthesis from Aniline

The experiment aimed to prepare acetanilide from aniline through nucleophilic acetylation using acetic anhydride and zinc dust. The procedure involved careful temperature control and recrystallization, resulting in a yield of 12.4 g of acetanilide with a percentage yield of 83.8% and a melting point of 114°C. Precautions were taken to ensure safety and proper reaction conditions due to the toxicity of aniline.

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9 views1 page

Acetanilide Synthesis from Aniline

The experiment aimed to prepare acetanilide from aniline through nucleophilic acetylation using acetic anhydride and zinc dust. The procedure involved careful temperature control and recrystallization, resulting in a yield of 12.4 g of acetanilide with a percentage yield of 83.8% and a melting point of 114°C. Precautions were taken to ensure safety and proper reaction conditions due to the toxicity of aniline.

Uploaded by

kpethar
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© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Experiment 2: Preparation of Acetanilide from Aniline

Aim: Prepare acetanilide by acetylating aniline with acetic anhydride, demonstrating nucleophilic
acetylation, purification by recrystallization, and determination of percentage yield.

Theory: Aniline reacts with acetic anhydride in the presence of zinc dust to form acetanilide through
nucleophilic acetylation. The amino group (-NH₂) acts as nucleophile, attacking the carbonyl carbon of
acetic anhydride. Zinc dust prevents oxidation of aniline. The reaction is:

C H NH + (CH CO) O → C H NHCOCH + CH COOH

Acetanilide crystallizes on cooling due to its lower solubility in cold water compared to hot water.

Materials Required: Aniline (10 mL), acetic anhydride (12 mL), zinc dust (0.5 g), distilled water, ice bath,
beakers (250 mL, 100 mL), glass rod, filter paper, Buchner funnel, vacuum pump, melting point apparatus.

Detailed Procedure:
Place 10 mL aniline in 250 mL beaker. Add 0.5 g zinc dust and 12 mL acetic anhydride slowly with
stirring. The reaction is exothermic. Maintain temperature below 50°C by placing beaker in cold water if
necessary. Stir vigorously for 15 minutes until reaction completes. Pour reaction mixture into 200 mL cold
water with stirring. White precipitate of crude acetanilide forms. Filter using Buchner funnel and wash
with cold water. Recrystallize by dissolving crude product in minimum hot water, filter hot solution, and
cool filtrate in ice bath. Collect pure crystals, dry, and weigh. Determine melting point (should be 113-
115°C).

Observations:
Mass of aniline taken = 10.2 g (density 1.02 g/mL). Mass of acetanilide obtained = 12.4 g. Theoretical yield
= (10.2/93) × 135 = 14.8 g. Percentage yield = (12.4/14.8) × 100 = 83.8%. Melting point observed = 114°C.

Precautions: Add acetic anhydride slowly to control exotherm. Use minimum water for recrystallization.
Cool slowly for larger crystals. Maintain proper anhydride to aniline ratio. Perform in fume hood due to
aniline toxicity.

Result: Prepared 12.4 g acetanilide with 83.8% yield and melting point 114°C, confirming purity.

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