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Please help with number 3 , thank you!

organle amount of 4-bromoacetanilide, which can be confirmed by TLC). Evaporate DCM using vacuum evaporator. Scrape the solid

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Answer #1

In the Synthesis of acetanilide, Sodium acetate is added for regeneration of aniline from its salt, because it is a weak base.

Sodium Hydroxide is not added for the regeneration of aniline from its salt in acetanilide synthesis, The reason is

Basically aniline is insoluble in NaOH. The Structure of aniline is an amine group -NH2 attached to the benzene ring. In the Principle stage the polarity of aniline is very low and the molecule is not charged. Because of its low polarity the molecule solubility in water is not possible, the reason is the insufficient interactions of water and the amino group .

The favourable intermediate will not obtained when Sodium Hydroxide is used for the regeneration of aniline from its salt. The resultant product will be meta-phenol aniline due to the meta addition of an hydroxy group to the aniline.

In a brief discussion, actually regeneration means to retrieve aniline back from the ion in the salt. That is to remove hydrogen ion. When it is done with Sodium Hydroxide

C6H5NH3+(aq) + OH-(aq)  ----------> C6H5NH2(l) + H2O(l)

Aniline is formed as tiny droplets spread out in water. It is insoluble in water. Aniline is a weak base.

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