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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 is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules of zinc at 400 °C: [22] C 6 H 5 OH + Zn → C 6 H 6 + ZnO. When phenol is treated with diazomethane in the presence of boron trifluoride (BF 3), anisole is obtained as the main product and nitrogen gas as a byproduct. C 6 H 5 OH + CH 2 N ...
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 ...
Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline.
The simplest aryl group is phenyl, which is made up of a benzene ring with one of its hydrogen atom replaced by some substituent, and has the molecular formula C 6 H 5 −. Note that a phenyl group is not the same as a benzyl group , the latter consisting of a phenyl group attached to a methyl group and a molecular formula of C 6 H 5 CH 2 − .
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. [3] Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one ...
The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring. For example, (C 6 H 5)(CH 3) 2 C + is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C 6 H 5 CH 2 •.
In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups (−OH) are substituted onto a benzene ring (C 6 H 6).These aromatic compounds are classed as phenols.