Q62E
Question
At what position, and on what ring, would you expect bromination of Benzanilide to occur? Explain by drawing resonance structures of the intermediates.
Benzanilide
Step-by-Step Solution
VerifiedThe attack occurs at the activated ring and yields ortho and para bromination products, mean position of substituent at ortho and para.
Bromination is the chemical reaction involving the reaction of a compound, and bromine results in bromine being added to the compund.The new product formed has different properties than initial one.
Treatment of benzanilide with bromine in the presence of catalyst FeBr3 results in the formation of ortho and para products as shown below:
Ortho and para bromination products of benzanilide
Attack occurs in the activated ring and yields ortho and para bromination products. The intermediate formed is resonance-stabilized by overlap of nitrogen lone pair electron with the pi-electron of the substituted ring.
Resonance structures of the Benzanilide at para position
Similar structures can be made of resonance forms of the intermediate resulting from ortho attack. Even though the nitrogen lone-pair electron are less available for delocalization than the lone pair of electrons of aniline. Because, the –NH group is nevertheless more activating than C=O group.