In an experiment, a student fully dissolves their unknown mixture (containing a neutral organic compound and acidic organic compound) in 35 mL of diethyl ether and quantitatively transfers this solution into their separatory funnel.

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2. But when the student starts to add the first portion of their aqueous extracting medium to their organic layer containing their 2 dissolved compounds, a precipitate (normally a white solid) forms in the separatory funnel. The precipitate that has formed is an ionic compound.  
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4. a. What is the precipitate that forms? 
5. i) Salt of conjugate acid of the neutral compound (N and Cl)
6. ii) Salt of conjugate acid of the acidic compound (AH2+ and Cl)
7. iii) Salt of conjugate base of the acidic compound (A and Na)
8. iv) NaCl
9. v) Salt of conjugate base of the neutral compound (N and Na)
10. b. What solvent should the student add to their separatory funnel to BEST dissolve the ionic compound?
11. i) water
12. ii) 10% HCl
13. iii) 10% NaOH
14. iv) Diethyl ether
15. c. Once adding the solvent into the separatory funnel what should the student do next?:
16. i) Drain the bottom layer immediately without shaking the funnel 
17. ii) Wait until three layers appear (one for each solvent added)
18. iii) Shake the separatory funnel to help the dissolving of the precipitate

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