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Aniline can react with bromine even in room temperatures in water. Acetyl chloride is added to prevent tribromination. The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline. The largest scale industrial reaction of aniline involves its alkylation with formaldehyde. An idealized ...
The carbylamine reaction ... Me 3 CNH 2 + CHCl 3 + 3 NaOH → Me 3 CNC + 3 NaCl + 3 H 2 O. Similar reactions have been reported for aniline. It is used to prepare ...
A white solid, it is the chloride salt of anilinium, which is the conjugate acid of aniline, C 6 H 5 NH 2. Anilinium chloride is produced by treatment of aniline with hydrochloric acid. The cation consists of a phenyl ring attached to a tetrahedral ammonium center. The C-N bond elongates from 1.41 Å in aniline to 1.474 Å in anilinium. [2]
This reaction goes by the German name Phenolverkochung ("cooking down to yield phenols"). The phenol formed may react with the diazonium salt and hence the reaction is carried in the presence of an acid which suppresses this further reaction. [33] A Sandmeyer-type hydroxylation is also possible using Cu 2 O and Cu 2+ in water.
With base, the reaction generates nitrite: NO + + 2 NaOH → NaNO 2 + Na + + H 2 O. As a diazotizing agent ... Reaction of nitrosonium with aniline to form a ...
Illustrative is the acetylation of aniline. First aniline is dissolved in water using one equivalent of hydrochloric acid. This solution is subsequently treated, sequentially, with acetic anhydride and aqueous sodium acetate. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion: Acetate then acts as a leaving group:
The reaction is faster at high pH. [2] Many other azo dyes have been prepared by similarly. Several procedures have been described in detail. [5] [6] [7] Naphthols are popular coupling agents. One example is the synthesis of the dye "organol brown" from aniline and 1-naphthol: Synthesis of organol brown from aniline and 1-naphthol
Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chloride provides acetanilide ( CH 3 −CO−NH−C 6 H 5 ). At high temperatures, aniline and carboxylic acids react to give anilides.