Exam+1+--Spring+2006+--+Blank - Spring 2006 Exam 1 I. (22...

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Methyl isocyanate is best repres ented by a group of three resona nce structures. Draw complete Lewis structures for each resonance contributor of methyl isocyana te. Follow the directions given in the boxes. Restrict your drawings to all closed-shell atoms with charges of +1, 0, -1 on each atom. Methyl isocyanate is not the only compound with a molecular formula of C 2 H 3 NO. Draw a structural isomer of methyl isocyanate thatcontains all closed- shell atoms and formal charges of zero on each atom. Name _______________________ Page 1 I. (22 points) A. C. D. In the presence of a catalyst, methyl isocyanate reacts with itself to form a cyclic trimer with no overall dipole moment. The ring contains six atoms . Draw the structure of this product. There are no other products. For an example of the formation of a different cyclic trimer, see below. Methyl isocyanate (connectivity: H 3 CNCO ) is a chemical used in the production of certain pesticides. It is very toxic. An accidental leakof this chemical in Bhopal, India in 1984 resulted in the deaths of 3800 people. Most signifi cant contributor Structural isomer of methyl isocyanate containing all closed shell atoms and zero f ormal charges. Least signifi cant contributor Intermediate contributor 3 CH 3 NCO catalyst Cyclic trimer with no molecular dipole moment. Consider all three resonance contributors above when choosing the most reasonable hybridization for all atoms, and provide an accurate and complete three-dimensional orbital picture f or the m a j o r resonance contributor of methyl isocyanate.
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This note was uploaded on 01/30/2011 for the course CHEM 210 taught by Professor Capolla during the Spring '07 term at University of Michigan.

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Exam+1+--Spring+2006+--+Blank - Spring 2006 Exam 1 I. (22...

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