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orgo 1 final - I(40 points Name Page 1 F.09.210FINAL An...

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Name_____________________________ I. (40 points) Page 1 F.09.210FINAL An unusual class of compounds was recently reported (J. Am. Chem. Soc. 2009, 131, 11875.) A possible resonance structure for the compound reported is shown below. B. Draw a resonance structure for Compound X that has no open shell atoms, no formal charges on any atom, and that is sp hybridized at the center carbon atom. Note, this resonance structure is a very minor contributor. N N C C C H H H H : C 1 C 2 N 1 H 1 H 2 C. Using hybridization arguments, explain why the resonance structure you drew in Part B is a very minor resonance contributor. If C1 were sp hybridized it would be predicted to be linear, but in this drawing it looks bent which would lead to strain. A. 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 Compound X. N C C C H H H H N E. Which would you predict to be the most acidic hydrogens? ( Circle one ): Hybridization Observable Geometry D. For the indicated atoms, C 1 , N 1 , C 2 , and N 2 , provide the hybridization and observable geometry: C 1 N 1 C 2 Hydrogen H 1 Hydrogen H 2 sp 2 trigonal planar sp 2 trigonal planar 2 8 6 2 2 2 N 2 sp 2 2 trigonal planar 2 sp 2 2 trigonal planar 2 N 2 2 N N C C C H H H H 8 Compound X Orbitals +4 Geometry +2 Charges/nbe +2 any sp3 or sp = zero pts sp AND linearity +3 strain +3 no partial no partial
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Name_____________________________ II. (40 points) Page 2 F.09.210FINAL H 3 CO H 3 CO H H 3 CO Cl 2, CH 3 OH H 3 CO H 3 CO + enantiomer B . The mechanism of Reaction N involves the formation of two cationic intermediates. In the boxes below, draw the structures of these two intermediates. Be sure to specify stereochemistry and provide the intermediates that form the product shown above. Reaction N Reaction O H 3 CO Cl + H H Cl H 3 CO H H H H 3 CO + Intermediate 1 in Reaction N Intermediate 2 in Reaction N C. Provide an explanation for the regioselectivity of this reaction. In other words, provide an explanation for the regioiselectivity of the reaction of intermediate 1 to form intermediate 2. Feel free to use pictures if useful.
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