First Exam Key - I(20 points Name Page 1(F.07.210E1p1 A The...

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Name _______________________ Page 1 (F.07.210E1p1) I. (20 points) The molecule shown below ( Compound NNO ) can be used to create plastics that release small amounts of NO into the blood stream, which prevents clotting, for instance, on medical devices that are implanted during surgery ( Org. Lett. 2007 , 9 , 3409). Understanding the actual structure of Compound NNO requires a set of four resonance structures (all atoms closed shell, all formal atomic charges -1, 0, +1). Use complete Lewis structures, showing all atoms, bonds, non-bonding electron pairs, and charges. (a) Draw the other three resonance structures for Compound NNO that meet these criteria. N C C N N O O H H H H H H Compound NNO W X Y Which of these 4 resonance forms is the most significant contributor to the overall structure of the actual molecule? (b) circle one: original NNO W X Y briefly state the reason: Considering the analysis of these resonance forms that you have done for part (b), circle the atom in this molecule that would be protonated most readily when treated with a Bronstead acid. (c) N C C N N O O H H H H H H based on the analysis of the resonance forms, circle the atom predicted to be protonated most easily; only the connectivity is shown so as not to prejudice your decision A. B. Cyanogen chloride is a low boiling colorless gas whose connectivity is Cl-CN. This compund is quite toxic, and was considered for use in chemical warfare because of its ability to cause injury to the eyes, nose, throat, and lungs. Even relatively small exposures can be fatal. Cyanogen chloride is prepared by the reaction between chlorine gas and sodium cyanide (see below). Using the curved-arrow convention, provide the arrows that describe the connectivity change(s) for the left-to-right reaction. Cl Cl Na C N + Cl Cl Na + C N C. When the reaction to prepare cyanogen chloride is carried out, an isomeric by-product called an isocyanide is formed. The connectivity for the isocyanide is ClNC. Provide the complete Lewis structure (containing all closed shell atoms, including formal charges as necessary) for ClNC.
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