Questions: 5. Below are the structures of three starting materials and final product for this reaction. If all four of these compounds were dissolved in an organic solvent, could you separate each of them individually using extractions? You have access to any concentrations of HCl or NaOH with a maximum concentration of 1.0 M for either. Be specific with your answer. If a compound could be isolated, state the specific concentration of aqueous solution and draw the structure of the ionized extracted compound. Hint 1: Use your pKa table! Hint 2: be careful with any compound that can undergo a chemical reaction of a substitution at a carbonyl, especially when using a base like NaOH . 2,6-dimethylaniline diethylamine chloroacetyl chloride Lidocaine

5. Below are the structures of three starting materials and final product for this reaction. If all four of these compounds were dissolved in an organic solvent, could you separate each of them individually using extractions? You have access to any concentrations of HCl or NaOH with a maximum concentration of 1.0 M for either. Be specific with your answer. If a compound could be isolated, state the specific concentration of aqueous solution and draw the structure of the ionized extracted compound. Hint 1: Use your pKa table! Hint 2: be careful with any compound that can undergo a chemical reaction of a substitution at a carbonyl, especially when using a base like NaOH . 2,6-dimethylaniline diethylamine chloroacetyl chloride Lidocaine
Transcript text: 5. Below are the structures of three starting materials and final product for this reaction. If all four of these compounds were dissolved in an organic solvent, could you separate each of them individually using extractions? You have access to any concentrations of HCl or NaOH with a maximum concentration of 1.0 M for either. Be specific with your answer. If a compound could be isolated, state the specific concentration of aqueous solution and draw the structure of the ionized extracted compound. Hint 1: Use your pKa table! Hint 2: be careful with any compound that can undergo a chemical reaction of a substitution at a carbonyl, especially when using a base like NaOH . 2,6-dimethylaniline diethylamine chloroacetyl chloride Lidocaine
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Solution

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Solution Steps

Step 1: Identify the compounds and their properties
  • 2,6-dimethylaniline: An aromatic amine with a basic nitrogen.
  • Diethylamine: A secondary amine, also basic.
  • Chloroacetyl chloride: An acid chloride, reactive and can hydrolyze in water.
  • Lidocaine: A complex molecule with both amine and amide functionalities.
Step 2: Determine the extraction strategy
  • Acid-Base Extraction: Utilize the basic nature of the amines and the acidic nature of the acid chloride.
  • pKa Consideration: Use pKa values to determine the appropriate pH for extraction.
Step 3: Separate 2,6-dimethylaniline
  • Extraction with HCl: Dissolve the mixture in an organic solvent and extract with 1.0M HCl. The 2,6-dimethylaniline will form a water-soluble hydrochloride salt.
  • Structure of Ionized Compound: \[ \text{2,6-dimethylaniline hydrochloride:} \quad \text{C}_8\text{H}_{11}\text{NH}_3^+ \text{Cl}^- \]

Final Answer

  1. 2,6-dimethylaniline can be separated by extraction with 1.0M HCl, forming its hydrochloride salt.
  2. Diethylamine and chloroacetyl chloride will remain in the organic phase.
  3. Lidocaine will also remain in the organic phase due to its neutral nature under these conditions.
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