1. Problem 1aNNHHHHHHHHHHHHProblem 1b a. (5 pts.) This is a neutral species. There are some electrons missing (nothing else is missing). Put the missing electrons on the structure to complete the structure. (Hint: computing the degrees of unsaturation might help.) b. (5 pts.) Above, draw a charge separated resonance structure of your complete Lewis structure of 1a. 2. Consider molecular formula: C14H4Cl10. a. (10 pts.) Compute the degrees of unsaturation. ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ b. (10 pts.) There is one ring in the structure. Could the structure possibly be aromatic? ____________________________________________________________________________ ____________________________________________________________________________ 3. (15 pts.) How are these two molecules related to each other? Do they have the same physical properties? ClCl4. Consider the molecule below. a. (10 pts.) Circle the weakest C-C bond in structure 4A below. 4A b. (10 pts.) At right above, draw a product of molecule 4A and NOOBrhv 5. Consider molecule 5A. a. (10 pts.) Below, draw the enantiomer of molecule 5A. Count the carbon atoms in your structure! 5AClHHH b. (10 pts.) Name 5A as a cyclohexane derivative. Stereochemistry! ____________________________________________________________________________ ____________________________________________________________________________6. (15 pts.) Draw the Diels –Alder product of O+CN Count your carbon atoms. Stereochemistry is important. 7. 7A 7B a. (5 pts.) How many 13C NMR in 7A. ____ b. (5 pts.) How many 13C NMR in 7B. ____ 8. (20 pts.) Draw the two highest-energy occupied molecular orbitals in 1,3-butadiene. Same question: draw only the occupied pi molecular orbitals of 1,3-butadiene. 9. (15pts.) Draw the product. HOOFOFF10. (20 pts.) Consider the reaction energy diagrams below. Use each letter only once. Rxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateABCDEF a. The diagram of the fastest reaction is __________ . b. The diagram that might represent the conversion of one enantiomer into another is __________ . c. The diagram that represents an endothermic reaction with one intermediate is __________ . d. The diagram that represents the twisting of a double through a dihedral angle of 180° starting from a cis-alkene and producing a trans-alkane is __________ . 11. (15 pts.) Predict the product. 1) (CH3CH2)2BH2) H2O2, NaOH(aq)Ether (solvent)Problem 1112. (10 pts.) Predict the product. 1) O32) H2O2, NaOH(aq)Ether (solvent)Problem 12 13. (10 pts.) Predict the product. 1) H3O(+)HeatwaterProblem
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