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Running the reaction: 1.25 of the p-bromoacetanilide and 10 mL of water were placed in a 100 mL round- bottomed flask After chilling the mixture in an ice bath for 15 minutes, 10 mL of concentrated sulfuric acid was added slowly (dropwise with a Pasteur pipette) A condenser was attached and the mixture was refluxed for 60 minutes The solution was allowed to cool down to room temperature TLC using hexane/ethyl acetate (8:2) as mobile phase shows a large spot very close to the starting line (RF0.08) and a very faint spot about halfway up (R=0.45) corresponding to the anilide Product isolation: The mixture was poured into 20 mL of ice-cold water and then slowly neutralized with 10 M NaOH (a total of 19 mL to get the pH=8) After cooing the mixture in an ice bath, it was extracted three times with 10 mL dichloromethane (the organic layer was the bottom layer) The combined organic layers were extracted with 20 mL of water and 20 mL of saturated sodium chloride solution After carefully separating the layers, the organic layer was dried over a minimum amount of anhydrous sodium sulfate The solvent was allowed to evaporate leaving behind a white solid, which was allowed to dry Product characterization: 0.71 g of the product М.р.: 63.5-65.3 °C

Running the reaction: 1.25 of the p-bromoacetanilide and 10 mL of water were placed in a 100 mL round- bottomed flask After chilling the mixture in an ice bath for 15 minutes, 10 mL of concentrated sulfuric acid was added slowly (dropwise with a Pasteur pipette) A condenser was attached and the mixture was refluxed for 60 minutes The solution was allowed to cool down to room temperature TLC using hexane/ethyl acetate (8:2) as mobile phase shows a large spot very close to the starting line (RF0.08) and a very faint spot about halfway up (R=0.45) corresponding to the anilide Product isolation: The mixture was poured into 20 mL of ice-cold water and then slowly neutralized with 10 M NaOH (a total of 19 mL to get the pH=8) After cooing the mixture in an ice bath, it was extracted three times with 10 mL dichloromethane (the organic layer was the bottom layer) The combined organic layers were extracted with 20 mL of water and 20 mL of saturated sodium chloride solution After carefully separating the layers, the organic layer was dried over a minimum amount of anhydrous sodium sulfate The solvent was allowed to evaporate leaving behind a white solid, which was allowed to dry Product characterization: 0.71 g of the product М.р.: 63.5-65.3 °C

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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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FIND THE PERCENTAGE YIELD, and include the moles of the reaction (part 3)

**Part 3:** **Running the reaction:** - 1.25 g of the p-bromoacetanilide and 10 mL of water were placed in a 100 mL round-bottomed flask. - After chilling the mixture in an ice bath for 15 minutes, 10 mL of concentrated sulfuric acid was added slowly (dropwise with a Pasteur pipette). - A condenser was attached and the mixture was refluxed for 60 minutes. - The solution was allowed to cool down to room temperature. - TLC using hexane/ethyl acetate (8:2) as mobile phase shows a large spot very close to the starting line (Rf=0.08) and a very faint spot about halfway up (Rf=0.45) corresponding to the anilide. **Product isolation:** - The mixture was poured into 20 mL of ice-cold water and then slowly neutralized with 10 M NaOH (a total of 19 mL to get the pH=8). - After cooling the mixture in an ice bath, it was extracted three times with 10 mL dichloromethane (the organic layer was the bottom layer). - The combined organic layers were extracted with 20 mL of water and 20 mL of saturated sodium chloride solution. - After carefully separating the layers, the organic layer was dried over a minimum amount of anhydrous sodium sulfate. - The solvent was allowed to evaporate leaving behind a white solid, which was allowed to dry. **Product characterization:** - 0.71 g of the product. - M.p.: 63.5-65.3 °C.
Transcribed Image Text:**Part 3:** **Running the reaction:** - 1.25 g of the p-bromoacetanilide and 10 mL of water were placed in a 100 mL round-bottomed flask. - After chilling the mixture in an ice bath for 15 minutes, 10 mL of concentrated sulfuric acid was added slowly (dropwise with a Pasteur pipette). - A condenser was attached and the mixture was refluxed for 60 minutes. - The solution was allowed to cool down to room temperature. - TLC using hexane/ethyl acetate (8:2) as mobile phase shows a large spot very close to the starting line (Rf=0.08) and a very faint spot about halfway up (Rf=0.45) corresponding to the anilide. **Product isolation:** - The mixture was poured into 20 mL of ice-cold water and then slowly neutralized with 10 M NaOH (a total of 19 mL to get the pH=8). - After cooling the mixture in an ice bath, it was extracted three times with 10 mL dichloromethane (the organic layer was the bottom layer). - The combined organic layers were extracted with 20 mL of water and 20 mL of saturated sodium chloride solution. - After carefully separating the layers, the organic layer was dried over a minimum amount of anhydrous sodium sulfate. - The solvent was allowed to evaporate leaving behind a white solid, which was allowed to dry. **Product characterization:** - 0.71 g of the product. - M.p.: 63.5-65.3 °C.
In this multi-step synthesis experiment, p-bromoaniline is synthesized from aniline through a series of reactions. Below are the detailed steps: **Equation 1:** - The starting compound is aniline, represented as a benzene ring with an amine group (NH₂). - When reacted with bromine (Br₂), it forms 2,4,6-tribromoaniline and other mono- and disubstituted products. The diagram illustrates tribrominated aniline with bromine atoms added to the 2nd, 4th, and 6th positions on the benzene ring. **Equation 2:** - Aniline reacts with acetic anhydride, depicted by two acyl groups attached by an oxygen, to form acetanilide. This conversion replaces the NH₂ group with an acetyl group (NHCOCH₃), forming a benzene ring bonded to NHCOCH₃. **Equation 3:** - Acetanilide undergoes bromination with Br₂. This results in p-bromoacetanilide, where a single bromine atom is added to the para position (opposite the acetylated amine). **Equation 4:** - The final step involves acid hydrolysis of p-bromoacetanilide. The acetyl group is removed, regenerating the amine group and resulting in p-bromoaniline, shown as a benzene ring with a bromine atom in the para position and an NH₂ group. These transformations demonstrate key principles of aromatic substitution and protective group chemistry in organic synthesis.
Transcribed Image Text:In this multi-step synthesis experiment, p-bromoaniline is synthesized from aniline through a series of reactions. Below are the detailed steps: **Equation 1:** - The starting compound is aniline, represented as a benzene ring with an amine group (NH₂). - When reacted with bromine (Br₂), it forms 2,4,6-tribromoaniline and other mono- and disubstituted products. The diagram illustrates tribrominated aniline with bromine atoms added to the 2nd, 4th, and 6th positions on the benzene ring. **Equation 2:** - Aniline reacts with acetic anhydride, depicted by two acyl groups attached by an oxygen, to form acetanilide. This conversion replaces the NH₂ group with an acetyl group (NHCOCH₃), forming a benzene ring bonded to NHCOCH₃. **Equation 3:** - Acetanilide undergoes bromination with Br₂. This results in p-bromoacetanilide, where a single bromine atom is added to the para position (opposite the acetylated amine). **Equation 4:** - The final step involves acid hydrolysis of p-bromoacetanilide. The acetyl group is removed, regenerating the amine group and resulting in p-bromoaniline, shown as a benzene ring with a bromine atom in the para position and an NH₂ group. These transformations demonstrate key principles of aromatic substitution and protective group chemistry in organic synthesis.
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