yoon_Aromaticitypracticeproblems - of allyl cation. energy...

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Practice problems for aromaticity (Ch 14) Chem 345 - Yoon 1 . Are the following compounds aromatic, antiaromatic, or neither? O O O N B CH 3 2 . Which of the following molecules would likely be planar, and which would be non-planar? Explain. O 3 . Which of the following compounds has the greater dipole moment? Explain. O O 4 . Compound A below undergoes S N 1 reaction with HCl at a rate significantly faster than that of compound B . Explain this observation. OH OH A B
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5. (More challenging) In this problem, you will derive the π molecular orbitals of cyclopropenyl cation from those of allyl cation. 1 2 3 1 2 3 a . On the left side of the following diagram, there are three orbital energy levels marked for the three π molecular orbitals of allyl cation. Next to each line, draw the bonding, non-bonding, and antibonding MOs
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Unformatted text preview: of allyl cation. energy cyclopropyl cation cyclopropenyl cation b. How many p-p bonding interactions are there in each MO? How many nodes? c. The π MOs of cyclopropenyl cation are like those of allyl cation, but there is an additional interaction between the p orbitals on carbons 1 and 3. Consider each MO of allyl cation. Is this additional interaction bonding, antibonding, or non-bonding? Will this cause the energy of the MO to go up or down in energy? d . How many degenerate π MOs should there be in cyclopropenyl cation? e . On the right side of the diagram, draw the π MOs of cyclopropenyl cation and indicate their approximate energies compared to those of allyl cation. Draw dotted lines to show how the MOs are related....
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yoon_Aromaticitypracticeproblems - of allyl cation. energy...

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