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Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C 6 H 5 OH. [5] It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C 6 H 5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause ...
The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pK a is usually between 10 and 12). Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion , and the corresponding salts are called phenolates or phenoxides ( aryloxides according ...
An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO 2 OH, are relatively stronger acids. Alcohols, with –OH, can act as acids but they are usually very weak.
Acid strength is the tendency of an acid, symbolised by the chemical formula, to dissociate into a proton, +, and an anion, . The dissociation or ionization of a strong acid in solution is effectively complete, except in its most concentrated solutions.
At pH = 10, phenol and phenolate are in approximately 1:1 proportions. The phenoxide anion (aka phenolate ) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines. [ 3 ]
Similar to other phenols, the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic. Each benzenediol can lose an H + from one of the hydroxyls to form a type of phenolate ion. The Dakin oxidation is an organic redox reaction in which an ortho - or para -hydroxylated phenyl aldehyde ( −CH=O ) or ketone ( >C=O ) reacts with ...
Substituent Name (in approximate order of deactivating strength) Structure Type of electronic effect Directing effect Strong trifluoromethylsulfonyl group [13]-SO 2 CF 3 –I, –M meta (substituted) ammonium groups [14]-NR 3 + (R = alkyl or H) –I nitro group-NO 2 –I, –M sulfonic acids and sulfonyl groups-SO 3 H, -SO 2 R cyano group-C≡N
It is often said the resonance stability of phenol makes it a stronger acid than that of aliphatic alcohols such as ethanol (pK a = 10 vs. 16–18). However, a significant contribution is the greater electronegativity of the sp 2 alpha carbon in phenol compared to the sp 3 alpha carbon in aliphatic alcohols. [7]