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Compare the orbital overlap in cycloprop...

Compare the orbital overlap in cyclopropane and alkane.

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As there is maximum overlap of orbitals along the bond axis, the covalent bond formation is strongest. In alkanes, there is perfect end on overlap of `sp^(3)` hybrid orbitals of C atoms. In cyclopropane, head on overlap of `sp^(3)` hybrid orbitals does not lead to ring closure because it requires bond angle of `109^(@)` , 28'. Therefore, in cyclopropane, overlap of `sp^(3)` hybrid orbitals is off the axis giving less effective bent ('banana') bonds.

In oprder to minimum the angle strain, the C atoms develop more p character in the orbitals forming the ring and consequently more s character in the external (C----H) bonds. Since bond angles obtained by overlapping p orbitals are `90^(@)` , additional p charactter, the hybrid orbitals for the external bonds are between `sp^(3)` and `sp^(2)` , leading to an increase in the bond angle. The more is the s character in the hybrid orbital used by C to form a bond, the shorter is the (C----H) bond, and hence the cyclopropane is more acidic than propoane.
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When the atomic orbitals overlap in such a way that their axis remain parallel to each other and perpendicular to the intermolecular axis this type of overlapping results the formation of

Knowledge Check

  • The angle strain in cyclopropane is :

    A
    `0^(@) 44'`
    B
    `24^(@) 44'`
    C
    `9^(@) 44'`
    D
    `5^(@) 16'`
  • The orbital overlapping is maximum in

    A
    `Cl_2`
    B
    `HI`
    C
    `HCl`
    D
    `HBr`
  • Type of orbital overlap in H_(2)O molecule is

    A
    `sp^(3) -sp^(3)`
    B
    `sp^(3) - 2p`
    C
    `sp^(2)-s`
    D
    `sp^(3) - s`
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