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According to another source, [13] a more controlled nitration of aniline starts with the formation of acetanilide by reaction with acetic anhydride followed by the actual nitration. Because the amide is a regular activating group the products formed are the para and ortho isomers.
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.
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%.
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]
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).
Acetanilides are compounds based on acetanilide, or N-phenylacetamide. Pages in category "Acetanilides" The following 68 pages are in this category, out of 68 total. ...
The nitration of the 2 position involves the loss of CO 2 as the leaving group. Desulfonation in which a sulfonyl group is substituted by a proton is a common example. See also Hayashi rearrangement. In aromatics substituted by silicon, the silicon reacts by ipso substitution.
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process: