1 8 CHEMISTRY 2211 EXAM 3 April 3, 2019 Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1. (9 pts) Provide the proper IUPAC names for the following compounds in the spaces provided below: SCORE 1. _________ 2. _________ 3. _________ 4. _________ 5. _________ 6. _________ 7. _________ 8. _________ 9. _________ 10. _________ 11. _________ 12. _________ 13. _________ 14. _________ Total: _______ Name __________________________________________________________________ Last, First 810#2 2. (10 pts) Provide a complete, detailed and stepwise mechanism for the following modified halohydrin reaction (haloether formation). In order to receive full credit, you must show all electron movement and provide all of the intermediates for this reaction. In addition, your intermediates must indicate proper stereochemistry where appropriate:3 3. (10 pts) Provide a complete, detailed and stepwise mechanism for the following acid catalyzed hydration reaction. In order to receive full credit, you must show all electron movement and provide all of the intermediates for this reaction. In addition, your intermediates must indicate proper stereochemistry where appropriate:4 4. (8 pts) Identify the indicated sets of protons as heterotopic, homotopic, enantiotopic, or diastereotopic:5 5. (14 pts) Draw all of the products formed in the following reactions. Make sure to indicate the proper regiochemistry and stereochemistry when necessary. In addition, indicate whether the product, or product mixture, is optically active by writing either YES or NO in the box provided:6 6. (4 pts) Rank the carbocations shown below in order of their increasing stability (1 = least stable, 4 = most stable): 7. (4 pts) Rank the alkenes shown below in order of their increasing stability (1 = least stable, 4 = most stable): 8. (4 pts) Draw skeletal structure(s) for the appropriate starting material(s) that will produce only the indicated products under the provided reaction conditions:7 9. (12 pts) Complete the following reaction schemes by adding the appropriate starting material(s), reagent(s), intermediate(s), and/or product(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary:8 10. (8 pts) Draw skeletal structures for the major product(s) of the following reactions. Be sure to indicate specific stereochemistry in your answers when necessary:9 11. (12 pts) On the reaction energy coordinate diagram provided below, clearly label each individual step’s activation energy (G‡) and the ΔG˚ of the overall reaction. Make sure that your labeling is neat and clear: Answer the following questions related to the reaction energy coordinate diagram provided above:10 12. (6 pts) Compound X, C9H18O2, has the 1H NMR, 13C NMR, and IR spectra shown below. Propose a structure that is consistent with the provided spectra. Calculate compound X’s degrees of unsaturation and write it in the box indicated below:1112 13. (4 pts) Compound K, C7H14O, has the 13C NMR spectrum shown below. Propose a structure that is consistent with the provided spectra:13 14. (5 pts) Match the individual peaks on the provided spectra with the hydrogens they represent in the structure below. Indicate your assignments by writing the appropriate letters in the corresponding
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