2083063830

2083063830 - conjugate base is more stable than...

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Weekly Quiz—February 3, 2006 1. Look at the following molecules. Give the hybridization, VSEPR shape and bond angle for the atoms marked with an asterisk. O Cl N * * * N H H * O Cl N * * * N H H * O has two e-prs sp3 hybridized Cl has three e-prs sp3 hybridized No free e-prs on N sp3 hybridized N has one free e-pr sp2 hybridized 2. In the following molecules, point out the (+) and (-) centers—partial or full. O OH Cl O O OH Cl O δ δ δ δ δ 3. Draw resonance structures for the following molecules. Draw the resonance hybrid. Do all your contributing structure equally contribute the resonance hybrid?
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O O
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O O O O O 1 Contributing structure ressulting from arrow 1 Contributing structure resulting from arrow 2 2 HYBRID : O δ δ δ δ δ HYBRID: δ δ δ
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O O O O HYBRID O δ δ δ δ 4. Phenol is more acidic than cyclohexanol—why? (Hint: Look at the resonance structures of the conjugate base formed). OH OH Phenol pKa=10 Cyclohexanol pKa=16 A more stable conjugate base increases the acid strength. This means that phenol’s
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Unformatted text preview: conjugate base is more stable than cyclohexanols. This is truethe conjugate base of phenol (called phenoxide) is stabilized by resonance. See below. O O O O O 5. Compare the dipole moments for CH 3 Cl, NaCl and benzene. Can you explain these differences in the molecular dipole? Which of these molecules are polar? Non-polar? NaCl has the strongest dipole, and benzene the weakest. The stronger dipole of NaCl is due to the larger charge separation between Na and Cl (basically a 1+ and 1- charge on Na and Cl, respectively). In benezene, there is small dipole for every C-H bond, but the net affect is a cancellation. CH 3 Cl has one bond with a large dipole, and thus it is the dominant feature in the overall dipole moment of the molecule. NaCl is an ionic compound; CH 3 Cl is polar; benzene is non-polar....
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This note was uploaded on 04/20/2008 for the course CHEM 231 taught by Professor Montaguesmith during the Spring '06 term at Maryland.

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2083063830 - conjugate base is more stable than...

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