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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 30VC

See similar textbooks

Related questions

Concept explainers

Question

100%

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

това до во ов
OH
ibuprofen
acetanilide
p-acetamidophenol
salicylic acid
OH
2
N
3
OH
4

Expert Solution

Trending now

This is a popular solution!

Step by step

Solved in 4 steps

SEE SOLUTION Check out a sample Q&A here

Follow-up Questions

Read through expert solutions to related follow-up questions below.

Follow-up Question

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

nothing will be in the organic layer

3 as a salt

Solution

by Bartleby Expert

SEE SOLUTION

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.