The intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline is benzyne.
The formation of aniline is take place in the presence of strong base, which is, sodium amide that abstracts the proton, followed by the loss of the bromine atom from the bromobenzene compound, makes the ring unstable and then it gets attacked by the nucleophile.
The reaction of bromobenzene with sodium amide, NaNH2 in the presence of liquid ammonia. We can see that the bromine atom which is attached to the benzene ring makes the hydrogen acidic which is present on the adjacent carbon atom.
The sodium amide which is a strong base abstracts the hydrogen which make ring acidic from the adjacent carbon atom to the bromine, which is, at the ortho-position. The resulting anion which is formed again loses the bromine atom (the leaving group).
Due to loss of proton and the loss of bromide ion, there will be two sp2 orbitals present in the ring, these overlap with each other and form a triple bond. An intermediate in reaction is formed called benzyne.
The benzyne intermediate is unstable and reactive. It acts as electrophilic in nature which is attacked by the strong nucleophile (NH2) which is present in the base (NaNH2/Liq.NH3).
Nucleophile (NH−2) can attack on the either side of the triple bond and the ammonia is a weak acid so, it donates its proton back to the benzene ring. So, we obtain a mixture of ortho- amino benzene and meta- amino benzene, which is, the aniline compound is formed.
Thus, we concluded that benzyne is intermediate formed in the reaction of formation of aniline.
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