a) From this flow chart, which acid is extracted when sodium bicarbonate is used as an extraction solvent? Explain, use knowledge of pKa, why this acid is extracted as opposed to the other acid present. b) What would be the end results if you first extract with NaOH, and then with NaHCO3? c) What would be the results after the addition of HCl to the NaOH extract and the NaHCO3 extracts?

Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter7: Extraction
Section: Chapter Questions
Problem 1Q
icon
Related questions
Question

a) From this flow chart, which acid is extracted when sodium bicarbonate is used as an extraction solvent? Explain, use knowledge of pKa, why this acid is extracted as opposed to the other acid present.

b) What would be the end results if you first extract with NaOH, and then with NaHCO3?

c) What would be the results after the addition of HCl to the NaOH extract and the NaHCO3 extracts? 

Mixture dissolved in organic solvent: dichloromethane
но
benzoic acid
2-naphthol
1,4-dimethoxybenzene
Extract with 25 mL of 10% NaHCO3 (3 times)
organic layer
aqueous layer = NaHCO3 extract
separate
Na*
HO
+
2-паphthol
1,4-dimethoxybenzend
sodium benzoate
Extract with 25 mL of 10% NaOH (3 times)
Place on ice
Add HCl until pH< 3
organic layer
aqueous layer = NaOH extract
Na* Cr
`OH
Na
sodium chloride
benzoic acid
1.4-dimethoxvbenzene
precipitate
aqueous
Add Na,(SO4)
Place on ice
Add HCl until pH < 3
Filter
Evaporate dichloromethane
Recyrstallize in methanol
HO
Na* Ch
sodium chloride
2-naphthol
Transcribed Image Text:Mixture dissolved in organic solvent: dichloromethane но benzoic acid 2-naphthol 1,4-dimethoxybenzene Extract with 25 mL of 10% NaHCO3 (3 times) organic layer aqueous layer = NaHCO3 extract separate Na* HO + 2-паphthol 1,4-dimethoxybenzend sodium benzoate Extract with 25 mL of 10% NaOH (3 times) Place on ice Add HCl until pH< 3 organic layer aqueous layer = NaOH extract Na* Cr `OH Na sodium chloride benzoic acid 1.4-dimethoxvbenzene precipitate aqueous Add Na,(SO4) Place on ice Add HCl until pH < 3 Filter Evaporate dichloromethane Recyrstallize in methanol HO Na* Ch sodium chloride 2-naphthol
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Sample Preparation in Analytical Chemistry
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.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:
9781305577190
Author:
Kenneth L. Williamson, Katherine M. Masters
Publisher:
Brooks Cole