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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.

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.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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.

 

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
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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