Name Last First 810 8 CHEMISTRY 2211 EXAM 3 April 3 2019 SCORE 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 1 9 pts Provide the proper IUPAC names for the following compounds in the spaces provided below 2 3 4 5 6 7 8 9 10 11 12 13 14 Total 1 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 2 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 3 4 8 pts Identify the indicated sets of protons as heterotopic homotopic enantiotopic or diastereotopic 4 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 5 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 6 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 7 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 8 11 12 pts On the reaction energy coordinate diagram provided below clearly label each individual step s activation energy G and the G 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 9 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 10 11 13 4 pts Compound K C7H14O has the 13C NMR spectrum shown below Propose a structure that is consistent with the provided spectra 12 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 boxes 13
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