orgo 1 exam 1 - I. (19 points) Name_ Page 1 F.09.210E1...

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I. (19 points) Page 1 F.09.210E1 Nitrous oxide is a colorless gas that is released from sewage treatment, soil management, and nylon production, among other sources. It is a greenhouse gas that has ~300 times more impact per unit weight than CO 2 . The stable form of N 2 O is a linear molecule with two major resonance structures. Like CO 2 , the molecular formula of nitrous oxide does not indicate its connectivity, which is NNO . A. Draw two resonances structures of N 2 O with all closed shell atoms and formal charges of -1/0/+1. B. Of the two structures you drew in the boxes above, which structure A or B contributes more to the overall structure of nitrous oxide and why? A. Negative charge on more electronegative oxygen atom. (Graders: note can be A or B, as long as correct structure is chosen). Note, in the unlikely event a student notes that there is greater strain in the allene structure vs. the alkyne structure that is also correct. N N O N N O C. Using lines, wedges, and dashes for sigma bonds, as well as indicating the directionality of non-bonding electron pairs, and using overlapped p-orbitals for ! -bonds as well as filled or empty lone p-orbitals as necessary, provide a three dimensional drawing for the structure you chose in Part B . H N N O D. N 2 O reacts with molecule C in the presence of a catalyst to give a product D and N 2 . Product D has the molecular formula C 8 H 10 O and some of its properties are listed below. Draw the structure of product D . N 2 O + Metal Catalyst Product D (C 8 H 10 O) N 2 + P r o d u c t D – 6 sp 2 hybridized carbon atoms – sp 2 hybridized oxygen – 1 H-bond donor – 1 H-bond acceptor – pK a = 11 OH ( C ) 4 3 3 5 4 A B -1 pt missing one or both formal charges -1 pt missing one or more nbe pairs all or nothing -1 pt missing one or both formal charges -1 pt missing one or more nbe pairs -1 pt missing one or both formal charges -1 pt missing one or more nbe pairs note: shaded orbitals are also fine. N
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orgo 1 exam 1 - I. (19 points) Name_ Page 1 F.09.210E1...

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