show the reaction of 4-methoxyaniline hydrochloride with ammonia. Indicate which layer (aqueous or organic) each component...

show the reaction of 4-methoxyaniline hydrochloride with ammonia. Indicate which layer (aqueous or organic) each component in the reaction will mainly eside in (For both products and reactants)

Expert Solution

The reaction taking place is the Aromatic Nucleophilic substitution reaction.

The nucleophile is the NH3. The ortho position ortho to -NH2Cl grouping is nucleophilic as NH2Cl grouping pulls electron density from ortho C by --ve Inductive effect. Also being meta to O-Me group it won’t get electron density from O-Me group.Hence this is the position that most likely to be attacked by nucleophile NH3.

4-Methoxy aniline hydrochloride forms as a treatment of aq. HCl acid on 4-Methoxy aniline, hence it exist in aqueous layer.

NH3 being polar molecule also exist in aqueous layer.

As reaction proceeds and 4-Methoxy aniline converts into the product 2-amino-4-methoxyaniline in presence of excess NH3. The product goes into the organic layer. (the product itself forms organic layer).

The reaction mechanism we can see in diagram.

queen_honey_blossom answered 2 years ago

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