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Additional%20problems%20before%20Quiz%203 - stable and...

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Additional problems before Quiz 3 Fall 2009 1. Both molecules have acidic protons. Which one has them potentially more acidic and why? H H H H 2. Explain the transformation (draw the mechanism): O NH 2 CH 3 O H OH N O CH 3 H 3. For each of the following compounds: a. determine the hybridization on the indicated atoms, b. show the kind of orbitals that overlap to form each bond c. show the number of unhybridized p orbitals on the indicated atoms H 3 C N H 3 C H H 3 C H 3 C CHO H 2 N CN 4. Indicate which structures are aromatic (A), antiaromatic (AA) or nonaromatic (NA). If aromatic or antiaromatic indicate number of electrons in closed loops : N S O N N N N N H N
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5. Draw the protonated structures for both molecules. Indicate which protonated structure is more
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Unformatted text preview: stable and explain why. O O 6. Explain (using B as comparison) why the pK a1 of A is so low and the pK a2 of A is so high. COOH COOH HOOC COOH pK a1 = 1.92 pK a2 = 6.23 pK a1 = 3.02 pK a2 = 4.39 A B 7. Indicate which structures are aromatic(A), antiaromatic(AA) or nonaromatic(NA). If aromatic or antiaromatic indicate number of electrons in closed loops: O O H N N N S 8. Explain why the acid on the left is stronger than the acid on the right: O O HOOC H H COOH 9. Explain the differences between pK a1 and pK a2 values for two dicarboxylic acids given below: COOH COOH COOH COOH pK a1 = 2.98 pK a2 = 5.28 pK a1 = 3.51 pK a2 = 4.82...
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