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However, the other effect called resonance add electron density back to the ring (known as the +M effect) and dominate over that of inductive effect. Hence the result is that they are EDGs and ortho/para directors. Phenol is an ortho/para director, but in a presence of base, the reaction is more rapid.
Groups with unshared pairs of electrons, such as the amino group of aniline, are strongly activating (some time deactivating also in case of halides) and ortho/para-directing by resonance. Such activating groups donate those unshared electrons to the pi system, creating a negative charge on the ortho and para positions. These positions are thus ...
The ortho effect also occurs when a meta-directing group is positioned in a meta arrangement relative to an ortho–para-directing group, a new substituent introduced into the molecule tends to preferentially occupy the ortho position relative to the meta-directing group rather than the para position.
Substrates containing two phenols (or an aniline and a phenol; see equation (8) below for a related example), undergo oxidative coupling in the presence of hypervalent iodine(III) reagents. Coupling of both the ortho and para positions is possible; however, the use of bulky silyl-protected phenols provides complete selectivity for para coupling ...
The ortho to para selectivity is low: [7] No reaction takes place when the solvent is replaced by tetrachloromethane. In contrast, when the reactant is 2-phenylethylamine, it is possible to employ relatively apolar solvents with exclusive ortho-regioselectivity due to the intermediate formation of a chloramine, enabling the Intramolecular reaction.
Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho-position of a direct metalation group or DMG through the intermediary of an aryllithium compound. [1] The DMG interacts with lithium through a hetero atom.
Phenol is a measurable component in the aroma and taste of the distinctive Islay scotch whisky, [58] generally ~30 ppm, but it can be over 160 ppm in the malted barley used to produce whisky. [59] This amount is different from and presumably higher than the amount in the distillate. [58]
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−O H) bonded directly to an aromatic hydrocarbon group. [1] The simplest is phenol, C 6 H 5 OH. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the ...