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Acetanilide crystals on a watch glass. Acetanilide is the organic compound with the formula C 6 H 5 NHC(O)CH 3. It is the N-acetylated derivative of aniline. [7] It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
The phrase ipso nitration was first used by Perrin and Skinner in 1971, in an investigation into chloroanisole nitration. [18] In one protocol, 4-chloro- n -butylbenzene is reacted with sodium nitrite in t -butanol in the presence of 0.5 mol% Pd 2 (dba) 3 , a biarylphosphine ligand and a phase-transfer catalyst to provide 4-nitro- n -butylbenzene.
The inductive and resonance properties compete with each other but the resonance effect dominates for purposes of directing the sites of reactivity. For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta).
The overall reaction mechanism, denoted by the Hughes–Ingold mechanistic symbol S E Ar, [3] begins with the aromatic ring attacking the electrophile E + (2a). This step leads to the formation of a positively charged and delocalized cyclohexadienyl cation, also known as an arenium ion, Wheland intermediate, or arene σ-complex (2b).
Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%.
The general mechanism for primary alkyl halides is shown below. [8] Mechanism of Friedel–Crafts alkylation. For primary (and possibly secondary) alkyl halides, a carbocation-like complex with the Lewis acid, [R (+)---(X---MX n) (–)] is more likely to be involved, rather than a free carbocation.
Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones , the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3 , which loses water in an elimination reaction to diazoiminium 5.
4-Nitroacetanilide is a chemical compound which is a nitro derivative of acetanilide. There are two other isomers of nitroacetanilide, 2-nitroacetanilide and 3-nitroacetanilide. 4-Nitroacetanilide is used as in intermediate in the production of some dyes. [2]