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Synthesis of p-Bromoaniline A student starts with 1.15 g of acetanilide and isolates 1.55 g of the product. Determine the percentage yield for the reaction. 1.15 g of the acetanilide and 4.8 mL acetic acid were placed in a 50 mL Erlenmeyer flask  2.80 mL of 4.1 M bromine in acetic acid (1:4) were added dropwise with a Pasteur pipette. product- 1.55 g of the product

Synthesis of p-Bromoaniline A student starts with 1.15 g of acetanilide and isolates 1.55 g of the product. Determine the percentage yield for the reaction. 1.15 g of the acetanilide and 4.8 mL acetic acid were placed in a 50 mL Erlenmeyer flask  2.80 mL of 4.1 M bromine in acetic acid (1:4) were added dropwise with a Pasteur pipette. product- 1.55 g of the product

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Synthesis of p-Bromoaniline

A student starts with 1.15 g of acetanilide and isolates 1.55 g of the product. Determine the percentage yield for the reaction.

1.15 g of the acetanilide and 4.8 mL acetic acid were placed in a 50 mL Erlenmeyer flask

 2.80 mL of 4.1 M bromine in acetic acid (1:4) were added dropwise with a Pasteur pipette.

product- 1.55 g of the product

 

**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:** - Depicts the reaction of aniline with bromine (Br₂), resulting in various mono- and disubstitution products. **Equation 2:** - Shows aniline reacting with acetic anhydride to form acetanilide. This transformation protects the amino group by converting it into an amide. **Equation 3:** - Describes the bromination of acetanilide. Bromine adds specifically to the para position relative to the amide group, creating p-bromoacetanilide due to steric hindrance and electronic effects. **Equation 4:** - Illustrates the acidic hydrolysis of the brominated amide, regenerating the amino group to produce p-bromoaniline. These equations collectively highlight the strategy of using protection and deprotection of functional groups to achieve selectivity in multi-step organic synthesis.
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:** - Depicts the reaction of aniline with bromine (Br₂), resulting in various mono- and disubstitution products. **Equation 2:** - Shows aniline reacting with acetic anhydride to form acetanilide. This transformation protects the amino group by converting it into an amide. **Equation 3:** - Describes the bromination of acetanilide. Bromine adds specifically to the para position relative to the amide group, creating p-bromoacetanilide due to steric hindrance and electronic effects. **Equation 4:** - Illustrates the acidic hydrolysis of the brominated amide, regenerating the amino group to produce p-bromoaniline. These equations collectively highlight the strategy of using protection and deprotection of functional groups to achieve selectivity in multi-step organic synthesis.
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