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Rearrangement of Carbocations...

Rearrangement of Carbocations

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How many 1,2-shifts are involved in the following rearrangement of carbocation?

The following transfonnation involves a carbocation rearrangement. The carbocation is generated by protonation of the hydroxyl group, followed by the loss of water. Which bond has to migrate in the carbocation to yield the product indicated (after the deprotonation)

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  • Under common reaction conditions, a carbocation rearranges to another carbocation of equal or greater stability. For example, a secondary carbocation will rearrange to a tertiary carbocation. It will not rearrange to a less stable primary carbocation. This generalization is not absolute, and because there is not a high energy barrier to the rearrangement of carbocations, rearrangement to a less stable cation can occur if it offers the chance to form a more stable product. In which of the following cations rearrangement takes place?

    A
    B
    C
    D
  • Under common reaction conditions, a carbocation rearranges to another carbocation of equal or greater stability. For example, a secondary carbocation will rearrange to a tertiary carbocation. It will not rearrange to a less stable primary carbocation. This generalization is not absolute, and because there is not a high energy barrier to the rearrangement of carbocations, rearrangement to a less stable cation can occur if it offers the chance to form a more stable product. In which of the following cations rearrangement takes place most rapidly?

    A
    B
    `CH_(3)-underset(underset(CH_(3))(|))overset(overset(H)(|))(C)-overset(oplus)(C)H_(2)`
    C
    D
  • Under common reaction conditions, a carbocation rearranges to another carbocation of equal or greater stability. For example, a secondary carbocation will rearrange to a tertiary carbocation. It will not rearrange to a less stable primary carbocation. This generalization is not absolute, and because there is not a high energy barrier to the rearrangement of carbocations, rearrangement to a less stable cation can occur if it offers the chance to form a more stable product. In the following cation, H//CH_(3) that is most likely to migrate to the positively charged carbon is : H_(3)C^(1)-underset(underset(OH)(|))overset(overset(H)(|))(""^(2)C)-underset(underset(H)(|))(overset(oplus)(""^(3)C))-underset(underset(CH_(3))(|))overset(overset(H)(|))(""^(4)C)-""^(5)CH_(3)

    A
    `CH_(3)" at "C-4`
    B
    H at C-4
    C
    `CH_(3)` at C-4
    D
    H at C-2
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    Whenever an intermediate carbocation is formed in reaction it may rearranges. Only those carbocation will rearrange which can produce more stable species . It can be done either by : (i) Shifting of H, alkyl , aryl, bond (1,2-shifting ) (ii) Ring expansion (iii) Ring contraction Most stable rearranged carbocation is is

    Statement-1: Carbocationic rearrangement is known as electrophilic rearrangement and Statement-2: Carbocations are stabilized by both hyperconjugation and +I effect.

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