Question

Will phthalimide dissolve in aqueous sodium bicarbonate?

Short answer

Answer: Yes, phthalimide will dissolve in aqueous sodium bicarbonate, producing the soluble salt phthalimidium carbonate.

Step-by-step solution

Identify the structure of phthalimide

Phthalimide is an imide compound with the structure shown below: C6H4(CO)2NH It has two carbonyl groups (C=O) and one nitrogen atom with two lone pairs, making phthalimide a weak base.

Identify the structure of sodium bicarbonate

Sodium bicarbonate is an ionic compound that consists of a sodium cation (Na+) and a bicarbonate anion (HCO3-). The bicarbonate anion is a weak acid, as it can donate a proton (H+) in an aqueous solution.

Determine the possible acid-base reaction

Now that we have identified the structures of phthalimide and sodium bicarbonate, let's consider the possible acid-base reaction between them. An acid-base reaction occurs when a proton (H+) is transferred from one molecule to another. In this case, the bicarbonate anion (HCO3-) could donate a proton to phthalimide. The possible reaction is as follows: C6H4(CO)2NH + HCO3- -> C6H4(CO)2NH2+ + CO3^2- Phthalimide, being a weak base, would accept a proton from the bicarbonate anion, forming a phthalimidium ion (C6H4(CO)2NH2+) and a carbonate ion (CO3^2-).

Assess the solubility of the reaction products

The phthalimidium ion (C6H4(CO)2NH2+) is a positively charged ion, and the carbonate ion (CO3^2-) is a negatively charged ion. The electrostatic attraction between these ions would lead to the formation of a soluble salt, phthalimidium carbonate (C6H4(CO)2NH2CO3). Sodium ions (Na+) from the sodium bicarbonate will remain in solution as spectator ions. In conclusion, phthalimide will dissolve in aqueous sodium bicarbonate through an acid-base reaction, producing the soluble salt phthalimidium carbonate.