"When a benzene ring bears enough strongly electron-withdrawing substituents, nucleophilic addition to give an intermediate anion with delocalized charge becomes feasible, followed by elimination of the leaving group (nucleophilic aromatic ipso substitution). Phenols result when the nucleophile is hydroxide ion, arenamines (anilines) when it is ammonia, and alkoxyarenes when alkoxides are employed. Very strong bases are capable of eliminating HX from haloarenes to form the reactive intermediate benzynes, which are subject to nucleophilic attack to give substitution products. Phenols may also be prepared by decomposition of arenediazonium salts in water and by Pd-catalyzed hydroxylations of haloarenes."
Quote Details
Added by wikiquote-import-bot
Unverified quote
0 likes
Original Language: English
Available Languages (1)
Sources
K. Peter C. Vollhardt, Neil E. Schore (2011) Organic chemistry : structure and function 6th ed. Ch. 22 : Chemistry of Benzene Substituents
https://en.wikiquote.org/wiki/Phenol
Revision History
No revisions have been submitted for this quote.
Categories
Phenol
2 quotes on TrueQuotesView all quotes by Phenol →
Related Quotes
"Phenols and their ethers are ubiquitous in nature; some derivatives have medicinal and herbicidal applications, where…"
"The question of a possible physiological significance, in the resemblance between the action of choline esters and th…"
"The α-hydrogens of nitroalkanes are appreciably acidic due to resonance stabilization of the anion … The anions deriv…"
"The most utilized Umpolung strategy is based on formyl and acyl anion equivalents derived from 2-lithio- 1,3-dithiane…"
"Alkyl halides are not often found in terrestrial organisms, but the kinds of reactions they undergo are among the mos…"
"Simple aromatic hydrocarbons come from two main sources: coal and petroleum. Coal is an enormously complex mixture ma…"
"Methylbenzene is readily metabolized because its methyl C – H bonds are relatively weak with respect to homolytic and…"
"The steric interaction between any axial substituent and a β-situated heteroatom is counted as zero. Thus, in 3-subst…"
"The alkaloids are bitter-tasting, natural nitrogen-containing compounds found particularly in plants. The name is der…"
"The electronic structure of the three heterocycles pyrrole, furan, and thiophene is similar to that of the aromatic c…"