UK CHE 230 - 6 Organic Chemistry CHE230-001 EXAM 1

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2006 Organic Chemistry CHE230-001 EXAM 1 Page 2 of 6 1. For the conformation of lowest energy estimate the atomic angles in the cation and the neutral molecule drawn below. Provide one number only for each question. CO O a. (5 pts.) C−O−C bond angle in cation. _______________________________ b. (5 pts.) C−O−C bond angle in neutral molecule. _________________________ c. (5 pts.) C−O−C−C dihedral angle in the cation. ___________ d. (5 pts.) C−O−C−C dihedral angle in the neutral molecule. ___________ The last two questions might be assisted by some Newman Projections. 2. (10 pts.) C8H6ClN has two rings. How many pi bonds does this formula have in its structure? Show your work. _______________________________________________________________________ __________________________________________________________________________2006 Organic Chemistry CHE230-001 EXAM 1 Page 3 of 6 3. FFFabc a. (5 pts.) How many 13C NMR signals from 3a? ___________ b. (5 pts.) How many 13C NMR signals from 3b? ___________ c. (5 pts.) How many 13C NMR signals from 3c? ___________ d. (5 pts.) Give a name for 3a : ____________________________________________________________________ e. (5 pts.) Give a name for 3c. There is stereochemistry to consider. : ____________________________________________________________________ 4. (10 pts.) 12345Below draw the Newman projection of the indicated molecule from the perspective shown. Sight down the C4−C3 bond. Choose the lowest-energy conformation.2006 Organic Chemistry CHE230-001 EXAM 1 Page 4 of 6 5. (10 pts.) Circle the most stable alkene and cross out the least stable alkene in the figure below. molecules for question 5. 6. (10 pts.) An acid is a reagent that is electron-poor or a molecule that can donate a proton. Consider the tetracyclic alkene below. Which molecular orbital in this molecule is most likely to provide electrons to react with an acid? Provide a reason. Short answer. Hint. The answer would be the same for any simple alkene. ____________________________________________________________________________________________________________________________________________________2006 Organic Chemistry CHE230-001 EXAM 1 Page 5 of 6 7. (10 pts.) Consider the reaction below in which an alkene is reduced to an alkane. Are the products likely lower in energy than the reactants (reaction equilibrium lies to the right) or does the reaction equilibrium lie to the left side of the equation? The reaction is heated and catalyzed because it does not happen spontaneously. Choose a position and support it with one or two sentences or a calculation from data in the table below. cat+ H2heat ____________________________________________________________________________________________________________________________________________________ ____________________________________________________________________________________________________________________________________________________ Table of bond energies in kcal /mol H–H : 104.2 C=C: 146 (double bond, pi and sigma) C–C: 83 H–C: 99 C–C: 65 (pi bond


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UK CHE 230 - 6 Organic Chemistry CHE230-001 EXAM 1

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