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The hydroxide will also deprotonate the phenol (4) to give a negatively charged phenoxide (5). The negative charge is delocalised into the aromatic ring, making it far more nucleophilic. Nucleophilic attack on the dichlorocarbene gives an intermediate dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H +) from a Brønsted–Lowry acid in an acid–base reaction. [1][2] The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or ...
The term enol is an abbreviation of alkenol, a portmanteaus deriving from "-ene"/"alkene" and the "-ol". Many kinds of enols are known. [1] Keto–enol tautomerism refers to a chemical equilibrium between a "keto" form (a carbonyl, named for the common ketone case) and an enol. The interconversion of the two forms involves the transfer of an ...
A Proton-coupled electron transfer (PCET) is a chemical reaction that involves the transfer of electrons and protons from one atom to another. The term was originally coined for single proton, single electron processes that are concerted, [1] but the definition has relaxed to include many related processes. Reactions that involve the concerted ...
In organic chemistry, the Hammett equation describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para- substituents to each other with just two parameters: a substituent constant and a reaction constant. [ 1 ][ 2 ] This equation was ...
The Bargellini reaction is a chemical reaction discovered in 1906 by Italian chemist Guido Bargellini. [1] The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution. [2] Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been ...
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 ...
The Nencki reaction (1881) is the ring acetylation of phenols with acids in the presence of zinc chloride. [24] In a green chemistry variation aluminium chloride is replaced by graphite in an alkylation of p-xylene with 2-bromobutane. This variation will not work with primary halides from which less carbocation involvement is inferred. [25]