Questions Explain how aniline is a base. Then explain how acetanilide is not bas

Question

Questions Explain how aniline is a base. Then explain how acetanilide is not basic even though it is produced from aniline. Hydrolysis of the acetic anhydride is a competing reaction to the amidization. Write a balanced equation for the hydrolysis reaction. With that reaction equation as a reference, how might the hydrolysis be minimized? Acetanilide is not particularly soluble in water. Why was the crystallization completed in an ice bath? How would this procedure be deter mental to the production of acetanilide?

Explanation / Answer

1. Aniline is a weak base. Aromatic amines such as aniline are much weaker bases than aliphatic amines because of the electron-withdrawing effect of the phenyl group. Aniline reacts with strong acids to form anilinium (or phenylammonium) ion (C6H5-NH3+).

Amides like acetanilide are not basic because electron density from the lone electron pair on the nitrogen is drawn away from the nitrogen atom towards the carbonyl carbon atom, which has a partial positive charge (while the carbonyl oxygen has a partial negative charge). One way to picture this is to draw a resonance structure of the amide such that there is a double bond from the carbonyl carbon to the N and a single bond from the same carbon to the oxygen; there will be a negative charge on the O and a positive charge on the N.

Another way to think of this is that since the carbonyl carbon has a partial positive charge, after protonation of the nitrogen, there will be a full positive charge and a partial positive charge on adjacent atoms on the same molecule, which is energetically unfavored.

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