4) In the previous problem you were asked to consider th
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4) In the previous problem you were asked to consider the hybridization of a carbocation whose geometry was constrained.
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4) In the previous problem you were asked to consider the hybridization of a carbocation whose geometry was constrained. It was concluded that "the empty orbital is a hybrid orbital, which makes this cation very high in energy." In this problem we want to better understand the meaning of this statement. Consider the orbital energies of hypothetical methyl cations constrained to planar (sp2) or tetrahedral (sp3) geometry (see diagram). Construct MO diagrams for each geometry. Based on the results of your MO analysis, check all the statements at the right that are true. Option 1. The positively charged carbon atom contributes four valence electrons to the molecular orbitals of the methyl cation. Option 2. The lowest unoccupied orbital for the planar methyl cation is an sp2 hybrid orbital. Option 3. The LUMO in the tetrahedral methyl cation is an sp3 hybrid orbital. Option 4. The LUMO in the tetrahedral methyl cation is lower in energy than the LUMO in the planar methyl cation. Option 5. The tetrahedral methyl cation is a stronger electrophile than the planar methyl cation. Option 6. The planar methyl carbon is more reactive than the tetrahedral methyl cation.
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