mechanism of hoffman bromamide reacn

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Initial Steps:

RCONH₂+Br₂+OH^-

first the base abstracts one proton from the amide(from nitrogen)

now Br_{2  fi}fissions heterolytically to give a Br⁺ which attacks the negatively charged N atom

giving RCONH-Br now due to the presence of -I group Br, the second hydrogen is even more acidic and further abstracted by base

giving RCON^--Br

Formation of alkyl isocyanate

there is rearrangement

Br leaves as Br^-  the alkyl group migrates from the carbon atom to nitrogen due to its resulting electron deficiency

leading to the formation of R-N=C=O

this is the intermediate alkyl isocyanate

this on hydrolysis gives amine

Hydrolysis

R-N=C=O

OH^- attacks the carbon (nucleophilic)

and leads to the formation of

now this is in resonance and has resonating structures

now the neg nitrogen behaves as  base and takes the proton from adjacent OH group

CO₂  then leaves and  forms

this again behaves as a bronsted base and abstracts a proton to form

 RNH_2......