First Exam Name PRINT Last First Chemistry 3332 Signature February 20 2004 ID Please circle class time Dr Bean s 10 00 AM Dr Bean s 1 00 PM Dr Bean s 4 00 PM Page Score 1 12 pts 2 20 pts 3 25 pts 4 14 pts 5 14 pts 6 15 pts TOTAL Note Present your student ID when you return the exam booklet A Nomenclature 12 points 4 each Give an acceptable name for each of the following compounds Be sure to indicate the stereochemistry where appropriate B Facts Total 20 points 1 Circle the compounds that would be stable i e unreactive in aqueous NaOH 6 points Note Points will be deducted for any incorrect circles 2 Place the following compounds in order of increasing reactivity in an SN1 process 1 least reactive 3 most reactive 6 points 3 Answer the following questions about the compound below Place the answers in the appropriately labeled boxes a How many distinct types of protons does the compound have b What are the theoretically predicted multiplicities splitting patterns of the signals for the protons labeled a and b c What is the multiplicity of the signal in the proton coupled 13C NMR spectrum for the carbon labeled c 8 points C Reactions Total 25 points 5 points each Please provide the starting material reagents or major product in the answer box Be sure your drawing indicates stereochemistry if applicable Partial credit is awarded only when intermediate products are shown below the reaction
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