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Final Examination Spr 2005

Final Examination Spr 2005 - Final Cumulative Examination...

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Final Cumulative Examination – CHEM 235 Spring 2005 Dr. James Poole Examination Instructions This examination is worth 250 points in your final grade of 1000 points. This examination will take up to 120 minutes, and consists of 10 questions, plus a bonus question. You may not be required to answer all components of a question, so read each question carefully . Note also that some questions are worth more than others: if a section of a question can be expected to be worth, say, 4 or more points; it should be obvious that a one word answer will not suffice For questions where you have made a choice of which section to answer, clearly indicate which sections you wish to have graded . After the examination, your graded laboratory reports and assignments will be available for collection. Note that any reports not collected after June 1 will be shredded. Note that the following may not be used in the examination: o Molecular modeling kits o Calculators, programmable or otherwise. o Computers, Mobile phones, personal organizers, or any other device capable of electronic storage of significant amounts of information, or remote access to the internet. o Textbooks, reference books, lecture notes or any other written material. Please ensure that mobile phones are turned off , and placed in a bag or pack prior to the start of the examination. Please do not turn this page over until instructed to do so by the examination proctor. Common Abbreviations : NBS N -bromosuccinimide DMF N,N -Dimethyl formamide BuLi n -butyllithium mCPBA m -chloroperbenzoic acid PCC Pyridinium chlorochromate THF tetrahydrofuran DMSO Dimethyl sulfoxide -OTs p -toluenesulfonate (tosylate) -TMS trimethylsilyl group -TBDMS tert -butyldimethylsilyl group 1
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Name Question 1 (10 points) Choose five of the eight compounds shown, and identify the class of compound to which these belong. N S S N N H N N BF 4 P Si O O OCH 2 CH 2 CH 3 O Question 2 (20 points) Give an example of the following: (a) A good nucleophile (b) A weak nucleophile (c) A poor or very weak nucleophile (d) A good leaving group (e) A reaction that converts a poor leaving group to a good leaving group (write the reaction) (f) An ylide (g) A protecting group (write the reaction, including the reaction conditions, that lead to the formation of this protecting group). 2
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