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Halogenation of a Substituted Benzene Ring
By: John Doe
CHEM 210(1 or 2, as appropriate)L – Lab Day (M, T, W, R, or F)
Date(s) Lab Performed (don’t forget any days you collected additional data.)
Sample Report (Be sure to Double Space your formal report)
Abstract
The purpose of this experiment was to halogenate a substituted benzene ring. Acetanilide, a
substituted benzene ring, was reacted with bromine in acetic acid and hydrobromic acid at
room temperature to prepare para-bromoacetanilide. A product was obtained in a yield of 0.12
g (86%) and with a melting point of 150-157 °C. An infrared spectrum of the product showed
bands at 3300, 1700, 1600 and 1500 wavenumbers (or use cm-1). A 1H NMR of the product
showed signals at 2.04, 7.45, 7.56, and 10.02 ppm. The halogenation of a substituted benzene
ring (acetanilide) with bromine was successful since parabromoacetanilide was obtained as
shown by melting point, infrared, and 1H NMR analysis.
Introduction
Get background from McMurry (and/or other referenced material) regarding the reaction that
was carried out. For example, who discovered it, significant intermediates, and/or why it is
important.1(show references after each new statement of fact)
Reaction (all rxns and mechanisms must be drawn by you and NOT shared)(sharing=cheating)
Give the overall chemical reaction with structures and names of all reactants and products.
Make sure you include the reaction conditions (solvent/temp/etc.) above and below the reaction
arrow. (Draw this using ChemDraw software) (Best to use this format once you open
ChemDraw: File-> Apply document settings from->ACS document 1996)
Mechanism
Be sure to draw the reaction mechanism (just as shown in class to be safe). Give the
mechanism specific to this reaction using structures and arrows. You must use the software
ChemDraw (or other chemical drawing software, but be sure it is neat and has good resolution.)
Results
Yield: 0.12 g, 0.56 mmol, 86%. Melting point: 150-157 ºC. IR: (thin film/NaCl) 3300 cm-1 (N-
H), 1700 cm-1 (C=O). 1H NMR (60 MHz, CDCl3 w/TMS) δ 2.04 (CH3, s, 3H), 7.45 (Ar-H, d,
J=8.34 Hz, 2H), 7.56 (Ar-H, d, J=8.34 Hz, 2H), 10.06 (N-H, broad s, 1H) ppm.
Theoretical yield: 0.090 g acetanilide (1 mol/135 g) (1 mol para-bromoacetanilide/ 1 mol
acetanilide) (214 g/mol) = 0.14 g para-bromoacetanilide. Percent yield: (0.12 g/0.14 g) 100% =
86%
Sample Report (Be sure to Double Space your formal report)
Discussion
The product yield was 0.12 g (86%). (Give some good reasons why your percent yield was
less than 100%. Think about the limitations inherent in the procedure as well as your own
limitations. Also, think about what you observed during the entire procedure that gives
evidence that product was lost.)
If there is evidence of significant impurity, based on any of your data, this evidence
must be discussed. For example, you must always discuss the melting point data: The melting
point of the product, 150 – 157 ºC, had a range of 7 ºC and was depressed 11 ºC from that of
the literature value for p-bromoacetanilide, 168 ºC3(where did you get the literature value?) indicating that
the product is impure.
The product was identified as p-bromoacetanilide based on the melting point, infrared
and 1H NMR data.
Conclusion
The purpose of this experiment, the halogenation of a substituted benzene ring, acetanilide,
with bromine was met since p-bromoacetanilide was obtained, as shown by melting point,
infrared and 1H NMR analysis. (or was it not confirmed by your results? Then say so)
References
1. McMurry, J. Organic Chemistry, 6th ed.; Brooks/Cole Publishing Co.; Pacific Grove,
2004, p number. (or pp numbers.)
Example for references – Dr. Brent Feske was the first to report this synthesis in 1999.1 (place the
superscript number after the period)(references should be in numerical order as they occur in the
written document)