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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 NH, Br Br Br2 Br plus mono-and disubstitution products Equation 2: NH, NH Equation 3: NH NH Br2 Br Equation 4: NH NH, Acid hydrolysis Br Br

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 NH, Br Br Br2 Br plus mono-and disubstitution products Equation 2: NH, NH Equation 3: NH NH Br2 Br Equation 4: NH NH, Acid hydrolysis Br Br

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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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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 NH, Br Br Br2 Br plus mono-and disubstitution products Equation 2: NH, NH Equation 3: NH NH Br2 Br Equation 4: NH NH, 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 NH, Br Br Br2 Br plus mono-and disubstitution products Equation 2: NH, NH Equation 3: NH NH Br2 Br Equation 4: NH NH, Acid hydrolysis Br Br
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