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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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