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    Free Radicals &carbocations

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    Omkar Kumar Jha
    The document discusses reactive intermediates such as free radicals and carbocations. It explains that carbocations are electrophilic due to having an electron deficient carbon, while carbanions are nucleophilic with a carbon containing a lone pair. Carbocation stability increases with the number of R groups bonded to the charged carbon atom. Free radicals form through homolytic bond cleavage and are short-lived and reactive species. Their relative stabilities follow the same trend as carbocations, being most stable when most substituted, due to stabilization through hyperconjugation. Examples of free radical reactions and their mechanisms are provided.

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    Free Radicals &carbocations

    Uploaded by

    Omkar Kumar Jha
    129 views13 pages
    The document discusses reactive intermediates such as free radicals and carbocations. It explains that carbocations are electrophilic due to having an electron deficient carbon, while carbanions are nucleophilic with a carbon containing a lone pair. Carbocation stability increases with the number of R groups bonded to the charged carbon atom. Free radicals form through homolytic bond cleavage and are short-lived and reactive species. Their relative stabilities follow the same trend as carbocations, being most stable when most substituted, due to stabilization through hyperconjugation. Examples of free radical reactions and their mechanisms are provided.

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    Free Radicals &Carbocations

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    The document discusses reactive intermediates such as free radicals and carbocations. It explains that carbocations are electrophilic due to having an electron deficient carbon, while carbanions are nucleophilic with a carbon containing a lone pair. Carbocation stability increases with the number of R groups bonded to the charged carbon atom. Free radicals form through homolytic bond cleavage and are short-lived and reactive species. Their relative stabilities follow the same trend as carbocations, being most stable when most substituted, due to stabilization through hyperconjugation. Examples of free radical reactions and their mechanisms are provided.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    129 views13 pages

    Free Radicals &carbocations

    Uploaded by

    Omkar Kumar Jha
    The document discusses reactive intermediates such as free radicals and carbocations. It explains that carbocations are electrophilic due to having an electron deficient carbon, while carbanions are nucleophilic with a carbon containing a lone pair. Carbocation stability increases with the number of R groups bonded to the charged carbon atom. Free radicals form through homolytic bond cleavage and are short-lived and reactive species. Their relative stabilities follow the same trend as carbocations, being most stable when most substituted, due to stabilization through hyperconjugation. Examples of free radical reactions and their mechanisms are provided.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 13

    CHE101 (B.Tech.

    Chemistry Course)

    Lecture - 25

    Reactive intermediates:Free Radicals &Carbocations


    Prepared By

    Dr. Harminder Singh

    Department of Chemistry Lovely Professional University, Phagwara, Punjab, India. E-mail: [email protected]

    Carbocation

    Cleavage of Covalent Bonds

    Carbocation

    Radicals and carbocations are electrophiles because they contain an electron deficient carbon. Carbanions are nucleophiles because they contain a carbon with a lone pair.

    Carbocation

    Structure of carbocation:

    Carbocations are classified as primary (1o), secondary (2o), or tertiary (3o), based on the number of R groups bonded to the charged carbon atom. As the number of R groups increases, carbocation stability increases.

    Carbocation

    More positive charge at C+ = a more unstable C+

    Carbocation

    Prepared by:Dr. Ashish Kumar 6

    Carbocation

    Carbocation Stability
    The order of carbocation stability is also a consequence of

    hyperconjugation. Hyperconjugation is the spreading out of charge by the overlap of an empty p orbital with an adjacent bond. This overlap (hyperconjugation) delocalizes the positive charge on the carbocation, spreading it over a large volume, and this stabilizes the carbocation. Example: CH3+ cannot be stabilized by hyperconjugation, but (CH3)2CH+ can.

    Prepared by:Dr. Ashish Kumar 7

    Free radicals

    Free Radicals:
    Homolytic bond cleavage leads to the formation of radicals

    (also called free radicals) Radicals are highly reactive, short-lived species Single-barbed arrows are used to show the movement of single electrons

    Production of Radicals Homolysis of relatively weak bonds such as O-O or X-X bonds can occur with addition of energy in the form of heat or light
    o or

    Free radicals Homolytic Bond Dissociation Energies and the Relative Stabilities of Radicals: The formation of different radicals from the same starting compound offers a way to estimate relative radical stabilities Examples: The propyl radical is less stable than the isopropyl radical

    \ Likewise the tert-butyl radical is more stable than the isobutyl radical

    Free radicals The relative stabilities of radicals follows the same trend as for carbocations The most substituted radical is most stable Radicals are electron deficient, as are carbocations, and are therefore also stabilized by hyperconjugation

    Free radicals
    Example of free radical Reaction:Chlorination of Methane: Mechanism of Reaction The reaction mechanism has three distinct aspects: Chain initiation, chain propagation and chain termination

    Mechanism:

    Chain termination

    Free radicals 2.Radical Addition to Alkenes: The anti-Markovnikov Addition of Hydrogen Bromide in presence of peroxide:

    Mechanism:

    Free radicals

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