Homework Help is Here – Start Your Trial Now!
Science
Chemistry
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

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.27P
See similar textbooks
icon
Related questions
Question

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 (R=0.08) and a very faint spot about halfway up (RF0.45) 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.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 (R=0.08) and a very faint spot about halfway up (RF0.45) 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.p.: 63.5-65.3 °C
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: NH2 NH Equation 3: `NH NH Br2 Br Equation 4: NH NH2 Acid hydrolysis Br Br
Transcribed Image Text: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: NH2 NH Equation 3: `NH NH Br2 Br Equation 4: NH NH2 Acid hydrolysis Br Br
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
SEE MORE TEXTBOOKS