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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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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Catalysis and Enzymatic Reactions
Catalysis is the kind of chemical reaction in which the rate (speed) of a reaction is enhanced by the catalyst which is not consumed during the process of reaction and afterward it is removed when the catalyst is not used to make up the impurity in the product. The enzymatic reaction is the reaction that is catalyzed via enzymes.
Lock And Key Model
The lock-and-key model is used to describe the catalytic enzyme activity, based on the interaction between enzyme and substrate. This model considers the lock as an enzyme and the key as a substrate to explain this model. The concept of how a unique distinct key only can have the access to open a particular lock resembles how the specific substrate can only fit into the particular active site of the enzyme. This is significant in understanding the intermolecular interaction between proteins and plays a vital role in drug interaction.
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Discuss the mechanism in a words.
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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