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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 alcohols is strongly affected by solvation. In the gas phase, alcohols are more acidic than in water. [35] In DMSO, alcohols (and water) have a pK a of around 29–32. As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the Williamson ether synthesis) in this solvent.
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 ...
Phenol ethers can be synthesized through an acid-catalyzed condensation of phenols and an alcohol. Phenols include phenol itself, benzenediols, polyphenols, and other phenol-derived molecules. An acid catalyzed condensation between phenol and ethanol, forming ethoxybenzene.
Ethanol is a neutral molecule and the pH of a solution of ethanol in water is nearly 7.00. Ethanol can be quantitatively converted to its conjugate base, the ethoxide ion (CH 3 CH 2 O −), by reaction with an alkali metal such as sodium: [79] 2 CH 3 CH 2 OH + 2 Na → 2 CH 3 CH 2 ONa + H 2. or a very strong base such as sodium hydride: CH 3 CH ...
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]
Phenol red exists as a red crystal that is stable in air. Its solubility is 0.77 grams per liter (g/L) in water and 2.9 g/L in ethanol. [1] It is a weak acid with pK a = 8.00 at 20 °C (68 °F). A solution of phenol red is used as a pH indicator, often in cell culture.
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.