Final answer:
To separate a mixture of KI, benzoic acid, naphthalene, and 1-adamantanamine, utilize liquid-liquid extraction by exploiting their differing solubilities and acid-base properties, isolating each compound step by step.
Step-by-step explanation:
Separating Components by Liquid-Liquid Extraction
To separate a mixture of potassium iodide (KI), benzoic acid, naphthalene, and 1-adamantanamine using liquid-liquid extraction, one can exploit the differences in solubility of these compounds in water and organic solvents. Considering the properties of each compound, a step-by-step extraction process can be outlined.
- Start with an aqueous solution containing all four compounds.
- Add an organic solvent that is immiscible with water, such as diethyl ether. Naphthalene and 1-adamantanamine, being nonpolar, will preferentially dissolve in the organic layer, while KI and benzoic acid will remain in the aqueous layer.
- Separate the two layers. The organic layer will now contain naphthalene and 1-adamantanamine.
- To the aqueous layer containing KI and benzoic acid, add a base such as sodium hydroxide (NaOH). This will deprotonate benzoic acid, forming its sodium salt, which is water-soluble and will remain in the aqueous layer, while KI is not affected.
- Separate the now basic aqueous layer from any remaining organic solvent. The basic aqueous layer contains the sodium salt of benzoic acid and KI.
- To recover benzoic acid, acidify the aqueous layer by adding hydrochloric acid (HCl), which will protonate the sodium benzoate back to benzoic acid. Benzoic acid will precipitate out since it is less soluble in water, especially at lower pH.
- Filter off the solid benzoic acid.
- The aqueous solution at this point contains only KI, which can be recovered through evaporation.
- Returning to the organic layer with 1-adamantanamine and naphthalene, the next step will be to exploit the basicity of 1-adamantanamine. Add an acid, such as hydrochloric acid (HCl), which will convert 1-adamantanamine into its water-soluble hydrochloride salt, leaving naphthalene in the organic layer.
- Separate the new aqueous layer containing 1-adamantanamine hydrochloride from the organic layer containing naphthalene.
- Evaporate the organic solvent to recover the naphthalene.
- Neutralize the aqueous layer containing 1-adamantanamine hydrochloride with a base to recover 1-adamantanamine, which can then be extracted with an organic solvent.
Through these steps, each component of the mixture can be successfully separated into individual components. The crucial aspect is understanding the solubility of each component in different solvents and their respective acid-base properties.