Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound.
Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound.
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Synthesis of p-Bromoaniline
The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply)
a) The compound has 98 % purity.
b) The sample is still wet.
c) The solid is impure.
d) The isolated compound in the target compound.
Transcribed Image Text:Experiment 6: Synthesis of p-Bromoaniline
Introduction
Since the amino group of aniline is a strong activator of the aromatic ring, direct bromination is
impractical because it leads to several products (equation 1) that are difficult to separate. To make
the desired product, the amino group needs to be protected as the acetamide, which also maintains
the direction of the incoming electrophile into ortho and para position. It slows down the rate of
reaction and introduces steric hindrance for the ortho positions (equation 2). Both factors lead to
an increased selectivity for the desired para product (equation 3). The acetamide can be hydrolyzed
back to the amine (equation 4). This strategy of protection and deprotection is a very important
tool in organic chemistry, especially in multi-step synthesis. In this experiment, p-bromoaniline
was synthesized in three steps starting from aniline.
Equation 1:
NH2
NH2
Br
Brz
plus mono-and disubstitution products
Equation 2:
NH3
NH
Equation 3:
NH
Brz
Equation 4:
NH
NH2
Acid hydrolysis
Br
Br
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