Question

You are given a dichloromethane solution containing compounds A,B, and C. You first extract with 3N...

You are given a dichloromethane solution containing compounds A,B, and C. You first extract with 3N NaOH and find that a salt of A is in the aqueous layer. Re‐extraction of the organic layer with 3N HCl leaves only C in the organic layer. Of the following, compound A is probably: a. hexane b. benzoic acid c. naphthalene d. sodium sulfate e. benzocaine

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Answer #1

The dichloromethane layer containing the three compounds was first extracted with 3 N NaOH solution and the salt of compound A was found in the aqueous layer. NaOH is a strong base and will react with both strong and weak acids to form a salt. The salt is definitely ionic, since sodium atom has a strong tendency to ionize; therefore, the salt is soluble in water due to ion-dipole interactions.

Of the given organic compounds, only (b) benzoic acid is an acid and will react with NaOH to form sodium benzoate, an ionic salt soluble in water. The reaction is as below.

C6H5CO2H (aq) + NaOH (aq) --------> C6H5CO2-Na+ (aq) + H2O (l)

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