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A mixture containing 1,3,5-trimethoxybenzene (A), phenol (B), aniline (C) and 1-naphthoic acid (D) was dissolved in...

A mixture containing 1,3,5-trimethoxybenzene (A), phenol (B), aniline (C) and 1-naphthoic acid (D) was dissolved in dichloromethane. Next two extractions wereperformed first using HCl then with NaOH. Which of the compounds could not beseparated in this procedure. Explain and show the pertinent reaction equation/s.

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Seperation of 1,3,5-trimethoxybenzene, phenol, aniline and 1-naphthoic acid by an extraction procedure он он NH2 aniline 1,3,

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