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  2. Free-radical addition - Wikipedia

    en.wikipedia.org/wiki/Free-radical_addition

    Free-radical reactions depend on one or more relatively weak bonds in a reagent. Under reaction conditions (typically heat or light), some weak bonds homolyse into radicals, which then induce further decomposition in their compatriots before recombination. Different mechanisms typically apply to reagents without such a weak bond.

  3. Buchner ring expansion - Wikipedia

    en.wikipedia.org/wiki/Buchner_ring_expansion

    The reaction mechanism of a Buchner ring expansion begins with carbene formation from ethyl-diazoacetate generated initially through photochemical or thermal reactions with extrusion of nitrogen. carbene mechanism. The generated carbene adds to one of the double bonds of benzene to form the cyclopropane ring. carbene insertion

  4. Friedel–Crafts reaction - Wikipedia

    en.wikipedia.org/wiki/Friedel–Crafts_reaction

    In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:

  5. Benzene - Wikipedia

    en.wikipedia.org/wiki/Benzene

    Benzene is sufficiently nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations to give substituted derivatives. Electrophilic aromatic substitution of benzene. The most widely practiced example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999. [73]

  6. Ortho effect - Wikipedia

    en.wikipedia.org/wiki/Ortho_effect

    There are three main ortho effects in substituted benzene compounds: Steric hindrance forces cause substitution of a chemical group in the ortho position of benzoic acids become stronger acids. Steric inhibition of protonation caused by substitution of anilines to become weaker bases, compared to substitution of isomers in the meta and para ...

  7. Electrophilic aromatic substitution - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_aromatic...

    The overall reaction mechanism, denoted by the Hughes–Ingold mechanistic symbol S E Ar, [3] begins with the aromatic ring attacking the electrophile E + (2a). This step leads to the formation of a positively charged and delocalized cyclohexadienyl cation, also known as an arenium ion, Wheland intermediate, or arene σ-complex (2b).

  8. Azide - Wikipedia

    en.wikipedia.org/wiki/Azide

    In chemistry, azide (/ ˈ eɪ z aɪ d /, AY-zyd) is a linear, polyatomic anion with the formula N − 3 and structure − N=N + =N −.It is the conjugate base of hydrazoic acid HN 3. Organic azides are organic compounds with the formula RN 3, containing the azide functional group. [1]

  9. Alkyne trimerisation - Wikipedia

    en.wikipedia.org/wiki/Alkyne_trimerisation

    An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal catalyst.The process is of historic interest as well as being applicable to organic synthesis. [1]