Chem 210- W07exam1Key - Name Page 1 I(22 points A Restless...

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Name _______________________ Page 1 I. (22 points) A. Restless Leg Syndrome, RLS, has been a disorder that has only recently made the news. One of the most commonly prescribed drugs for RLS is ropinirole, sold as Requip™. Analyze the structure and potential reactivity of this compound, considering all other closed shell resonance contributors in your evaluations. Requip (ropinirole) (a) For each of the atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic geometry (VSEPR), and observable geometry (shape). no partial credit Atom 1 N O H N Atom 2 Atom 3 Atom 4 Atom 4 Atom 2 Atom 3 Atom 1 Hybridization Electronic (VSEPR) geometry observable geometry BOND C BOND A BOND D BOND E BOND B sp3 trig pyramid tetrahedral tetrahedral tetrahedral sp3 sp2 sp2 trig planar trig planar none trig planar 2 2 2 2 b) List the bonds indicated (in Requip, above) in order of their lengths - if any are predicted to be exactly the same length, put them together in the same box: no partial credit longest shortest E B D C A 5 c) Your bloodstreamhas a fairly constant pH of about 7. If Requip was placed in your bloodstream, would it exist in the form shown above ( circle Yes or No )? Explain BRIEFLY, indicating specific atom(s) in Requip to justify your answer. it will be protonated in the bloodstream at atom 4 the NH+ would have a pka of approximately 9.4 circle one Yes No Requip would be in this form at pH 7 3 d) Two of the major buffer systems present in your bloodstream are derived from phosphoric acid and carbonic acid; both are shown in their fully protonated forms below. Given the pKa information provided, draw the form(s) of these molecules that would predominate in your blood at pH 7.0. C O O O H H ii) Carbonic acid 2 acidic protons pKas: 6.5 and 10.2 P O O O H H i) phosphoric acid 3 acidic protons pKas: 2, 7 and 12 O H P O O O H O H P O O O H O C O O O H predominant form(s) that exist in blood at pH 7 predominant form(s) that exist in blood at pH 7 3 3 any two atoms negative any one O atom negative one O atom negative AND
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Name _______________________ Page 2 II. (22 points) Some metals, like iron (Fe), behave in a way that is very similar to boron - they are considered open- shelled. The following transformation involves a complexation (Lewis acid/base) reaction followed by a decomplexation. The complete transformation yields a resonance stabilized organic product (called
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