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What is the mechanism for the preparation of 4-bromoacetanilide from acetanilide and bromine, and how does the mechanism differ from the preparation of aniline from nitrobenzene?

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The preparation of 4-bromoacetanilide from acetanilide and bromine involves electrophilic aromatic substitution  EAS  reaction, while the preparation of aniline from nitrobenzene involves a reduction reaction. Here are the mechanisms for both reactions:1. Preparation of 4-bromoacetanilide from acetanilide and bromine:Step 1: Formation of the electrophileBromine  Br2  reacts with a Lewis acid catalyst, such as aluminum bromide  AlBr3  or iron III  bromide  FeBr3 , to form the electrophile, bromonium ion  Br+ .Br2 + AlBr3/FeBr3  Br+ + AlBr4-/FeBr4-Step 2: Electrophilic attack on the aromatic ringThe electrophile, Br+, attacks the aromatic ring of acetanilide, which is activated by the electron-donating amino group  -NHCOCH3  at the para position. This leads to the formation of a sigma complex, with a positive charge on the carbon atom.Step 3: Deprotonation and regeneration of the catalystA base, usually the halide ion  Br-  formed in step 1, abstracts a proton from the sigma complex, resulting in the formation of 4-bromoacetanilide and regenerating the Lewis acid catalyst.2. Preparation of aniline from nitrobenzene:The conversion of nitrobenzene to aniline involves a reduction reaction, which can be carried out using various reducing agents, such as hydrogen gas  H2  in the presence of a metal catalyst  e.g., palladium on carbon , or using tin  Sn  and hydrochloric acid  HCl .Step 1: Reduction of the nitro groupThe nitro group  -NO2  in nitrobenzene is reduced to an intermediate hydroxylamine derivative  -NHOH  by the reducing agent.Step 2: Further reduction and protonationThe hydroxylamine derivative is further reduced to form an amine group  -NH2 , which then gets protonated to form aniline.In summary, the preparation of 4-bromoacetanilide from acetanilide and bromine involves an electrophilic aromatic substitution reaction, while the preparation of aniline from nitrobenzene involves a reduction reaction. These two mechanisms are fundamentally different in terms of the type of reaction and the intermediates involved.

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