Interpretation:
A stepwise procedure with equations to show how to separate a mixture of
Concept Introduction:
Separation of the components of a mixture of organic compounds is based on the difference in their solubility in water and an organic solvent immiscible with water.
Advantage is taken of the difference in solubility of a basic (or acidic) compound and its conjugate base (or acid) in water.
Conjugate base of an acid or conjugate acid of a base are salts. Their ionic nature leads to a higher solubility in water as compared to a non-polar (or weakly polar) organic solvent. They are extracted into the aqueous phase containing an acid or a base from the solution of the mixture in a suitable organic solvent such as diethyl ether.
The base or the acid can then be recovered from the aqueous phase by neutralizing the conjugate acid (or base) with a strong base such as sodium hydroxide (or a strong acid such as hydrochloric acid). The recovered base (or acid) being insoluble separates out.
A neutral compound remains in ether solution (organic phase) from which it can be recovered by allowing ether to evaporate.
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Chapter 22 Solutions
CAREY: ORGANIC CHEMISTRY
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- You could extract caffeine from neutral organics by treatment with aqueous HCl (acid). Write the structure of the conjugate acid of caffeine (after treatment with HCl) and explain why it would dissolve in the aqueous layer.arrow_forwardAs a group, use your knowledge of acid-base extraction to come up with a plan to separate the following compounds from each other. Your plan should include specific solvents or reagents to be used and result in 4 isolated solids in the end. p-anisidine pyrene salicylic acid 2,3-xylenolarrow_forwardAn organic was subjected to sodium fusion and the resulting Lassaigne’s extract boiled with FeSO4 and acidified with concentrated H2SO4, yielding a Prussian blue color. Give an example of a compound fits this description?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning