Dawson College
Department of Chemistry & Chemical Technology
Laboratory Report
Organic Chemistry
Experiment #7
Experiment Title: Bromination of Acetanilide
Written by:
Jenna Yaphe, 2337769
Partner:
Shaina Balyasnyy
Date of the Experiment: Wednesday, 20 November 2025
Date of the Lab Report Submission: Wednesday, 27
November 2025
Reaction scheme:
Table of reagents:
Compound
Molar Mass
(g/mol)
Density
(g/mL)
Amount
(g)
Moles
Acetanilide
135.16
1.22
0.50 g
0.00370
Glacial Acetic
Acid
60.052
1.049
2.0 ml
0.03494
Bromine in Acetic
Acid
159.81
3.111
10 ml
0.19467
Ethanol
46.068
0.79
10 ml
0.17149
Data and results:
1. Mass of acetanilide used
0.5000 g
2. Moles of acetanilide used
0.003694 mol
3. Mass of product obtained after recrystallization
0.1705 g
4. Percent yield
34.10%
5. Melting point of the product
171-173 C
6. Identification of the product formed
4- bromoacetanilide
Sample calculations:
1. Calculate the moles of acetanilide used
0.500𝑔
1 𝑚𝑜𝑙
𝑥 135.16 𝑔 = 0. 003694
2. Calculate percent yield
Post lab:
4) 4- Bromoacetanilide, otherwise known as the para product, is the only product obtained.
The discrepancy is due to steric hindrance that is present in the 3- Bromoacetanilide/ ortho
position. The para position is the only product formed since it does not cause any steric
hindrance.
5) When phenol reacts with excess bromine, it forms 2,4,6-tribromophenol through a
substitution reaction that preserves the aromaticity of the benzene ring. The hydroxyl group
(-OH), being a smaller ortho/para-directing group, allows for higher reactivity at the ortho
and para positions compared to the bulkier acetamide group in acetanilide. In other words, the
excess bromine leads to bromination at both ortho positions and the para position, producing
the fully substituted product. (information taken from references 3 and 4)
Raw data sheet
References
1. Department of Chemistry. (2021). Organic Chemistry: Laboratory experiments.
Experiment #7. Electrophilic Aromatic Substitution: Bromination of Acetanilide.
pp.37-40. Dawson College. Montreal.
2. National Library of Medicine, National Center for Biotechnology Information.
[Online]. Available:
https://pubchem.ncbi.nlm.nih.gov/docs/contact, Accessed November 4, 2024.
3. Ring Reactions of Phenol, www.chemguide.co.uk/organicprops/phenol/ring.html.
Accessed 26 Nov. 2024.
4. “Ring Reactions of Phenol.” Chemistry LibreTexts, Libretexts, 23 Jan. 2023,
chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organi
c_Chemistry)/Phenols/Reactivity_of_Phenols/Ring_Reactions_of_Phenol.