ily has a mixture of 4 compounds that they want to separate. All 4 compounds appear as white solid powders. When Lily adds 25 mL of chloroform (density = 1.492 g/mL; bp = 61C) to the mixture, everything dissolves with stirring. Lily decides to use acid-base extraction to separate the compounds from one another. Chloroform and water are immiscible, and all acids and bases will be prepared in water. 1. First, Lily tries extracting the organic solution with 1.0 M HCl (20 mL). Which layer will be the organic layer in the separatory funnel? - top layer -bottom layer - only one layer 2. What will be in the organic layer after the extraction with 1.0 M HCl? - 1,3,4 -2 only -1,2,3,4 -nothing will be left in organic layer 3. Lily sets the first aqueous layer aside and returns the organic layer to the separatory funnel. Next, they choose to extract with 0.50 M NaOH (20 mL). What will be left in the organic layer after this step? -1,3,4 -2,3 -1,3,4 as salts -2 only 4. What should the pH of the water be after Lily combines the two aqueous layers? - greater than 7 -7 -less than 7 5. Calculate the pH of the aqueous combined aqueous layers. Remember that pH = - log[H+] where the concentration is in M. 6. After combining the two aqueous layers and adjusting the pH to 2, Lily observes solid precipitate out of solution. They cool it in an ice bath and then collect the solid by vacuum filtration. What is this solid? - 1,4 as salts - 1,3,4 as salts -1,4 -1,3,4 7. Lily realizes that the solid they have collected is not a pure compound but a mixture. They re-dissolve it in 25 mL of chloroform and try extracting with 5% NaHCO3 (20 mL) instead. What will be in the aqueous layer after this step? -3,4 as salts -1,3,4 as salts -3 as a salt -1,4 as salts 8. Will anything be left from the organic layer after Lily dries it and evaporates off the solvent? - nothing will be left -3 -3 as a salt -2 9. How could 1 and 4 be separated from each other? (IMAGE INCLUDED) - Re-dissolve in chloroform and extract with HCl - Re-dissolve in chloroform and extract with NaHCO3 - They cannot be separated from each other with acid-base extraction - Re-dissolve in chloroform and extract with NaOH

ily has a mixture of 4 compounds that they want to separate. All 4 compounds appear as white solid powders. When Lily adds 25 mL of chloroform (density = 1.492 g/mL; bp = 61C) to the mixture, everything dissolves with stirring. Lily decides to use acid-base extraction to separate the compounds from one another. Chloroform and water are immiscible, and all acids and bases will be prepared in water. 1. First, Lily tries extracting the organic solution with 1.0 M HCl (20 mL). Which layer will be the organic layer in the separatory funnel? - top layer -bottom layer - only one layer 2. What will be in the organic layer after the extraction with 1.0 M HCl? - 1,3,4 -2 only -1,2,3,4 -nothing will be left in organic layer 3. Lily sets the first aqueous layer aside and returns the organic layer to the separatory funnel. Next, they choose to extract with 0.50 M NaOH (20 mL). What will be left in the organic layer after this step? -1,3,4 -2,3 -1,3,4 as salts -2 only 4. What should the pH of the water be after Lily combines the two aqueous layers? - greater than 7 -7 -less than 7 5. Calculate the pH of the aqueous combined aqueous layers. Remember that pH = - log[H+] where the concentration is in M. 6. After combining the two aqueous layers and adjusting the pH to 2, Lily observes solid precipitate out of solution. They cool it in an ice bath and then collect the solid by vacuum filtration. What is this solid? - 1,4 as salts - 1,3,4 as salts -1,4 -1,3,4 7. Lily realizes that the solid they have collected is not a pure compound but a mixture. They re-dissolve it in 25 mL of chloroform and try extracting with 5% NaHCO3 (20 mL) instead. What will be in the aqueous layer after this step? -3,4 as salts -1,3,4 as salts -3 as a salt -1,4 as salts 8. Will anything be left from the organic layer after Lily dries it and evaporates off the solvent? - nothing will be left -3 -3 as a salt -2 9. How could 1 and 4 be separated from each other? (IMAGE INCLUDED) - Re-dissolve in chloroform and extract with HCl - Re-dissolve in chloroform and extract with NaHCO3 - They cannot be separated from each other with acid-base extraction - Re-dissolve in chloroform and extract with NaOH

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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Lily has a mixture of 4 compounds that they want to separate. All 4 compounds appear as white solid powders. When Lily adds 25 mL of chloroform (density = 1.492 g/mL; bp = 61C) to the mixture, everything dissolves with stirring. Lily decides to use acid-base extraction to separate the compounds from one another. Chloroform and water are immiscible, and all acids and bases will be prepared in water.

1. First, Lily tries extracting the organic solution with 1.0 M HCl (20 mL). Which layer will be the organic layer in the separatory funnel?

- top layer

-bottom layer

- only one layer

2. What will be in the organic layer after the extraction with 1.0 M HCl?

- 1,3,4

-2 only

-1,2,3,4

-nothing will be left in organic layer

3. Lily sets the first aqueous layer aside and returns the organic layer to the separatory funnel. Next, they choose to extract with 0.50 M NaOH (20 mL). What will be left in the organic layer after this step?

-1,3,4

-2,3

-1,3,4 as salts

-2 only

4. What should the pH of the water be after Lily combines the two aqueous layers?

- greater than 7

-7

-less than 7

5. Calculate the pH of the aqueous combined aqueous layers. Remember that pH = - log[H+] where the concentration is in M.

6. After combining the two aqueous layers and adjusting the pH to 2, Lily observes solid precipitate out of solution. They cool it in an ice bath and then collect the solid by vacuum filtration. What is this solid?

- 1,4 as salts

- 1,3,4 as salts

-1,4

-1,3,4

7. Lily realizes that the solid they have collected is not a pure compound but a mixture. They re-dissolve it in 25 mL of chloroform and try extracting with 5% NaHCO3 (20 mL) instead. What will be in the aqueous layer after this step?

-3,4 as salts

-1,3,4 as salts

-3 as a salt

-1,4 as salts

8. Will anything be left from the organic layer after Lily dries it and evaporates off the solvent?

- nothing will be left

-3

-3 as a salt

-2

9. How could 1 and 4 be separated from each other? (IMAGE INCLUDED)

- Re-dissolve in chloroform and extract with HCl

- Re-dissolve in chloroform and extract with NaHCO3

- They cannot be separated from each other with acid-base extraction

- Re-dissolve in chloroform and extract with NaOH

The image contains chemical structures of four different compounds, each labeled with a number and name:

1. **Ibuprofen**:

This structure shows a benzene ring attached to an isobutyl group (on the left) and a propanoic acid group (on the right). It is a widely used nonsteroidal anti-inflammatory drug (NSAID).

2. **Acetanilide**:

The structure features a benzene ring with an acetamido group directly attached. It is an organic compound formerly used as a pain reliever and fever reducer.

3. **p-Acetamidophenol (Paracetamol or Acetaminophen)**:

Here, the benzene ring is attached to an acetamido group and a hydroxyl group at the para position (opposite sides of the benzene ring). This compound is commonly used as a pain reliever and fever reducer.

4. **Salicylic Acid**:

This compound consists of a benzene ring with a carboxylic acid group and a hydroxyl group in the ortho position (adjacent). It is used in various medicinal formulations, particularly in skincare and as an anti-inflammatory agent.

The diagrams provide a visual representation of the chemical structure, highlighting functional groups and molecular connectivity.

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Will anything be left in this new organic layer (from Q20)?

nothing will be in the organic layer

3 as a salt

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