Final Exam 235 Spr 2004

Final Exam 235 Spr 2004 - CHEM235 May 07, 2004 Final...

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CHEM235 Final Cumulative Examination May 07, 2004 Examination Instructions The examination is worth 200 points in a total of 800 points for this course. This examination lasts 120 minutes, and consists of 8 questions. Note that some questions do not require you to answer all of the sections. Read the questions carefully before attempting them. 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. 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 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 Dimethyl formamide LDA Lithium diisopropylamide BuLi n -butyllithium mCPBA m -chloroperbenzoic acid PCC Pyridinium chlorochromate -OTs p -toluenesulfonate (tosylate) group -TMS trimethylsilyl group -TBDMS tert -butyldimethylsilyl group -Ph Phenyl group
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Question 1 (10 points) Identify the class of compound to which the following compounds belong ( ie . identify their functional groups): N OH S O O CH 3 O O O O N N Cl Question 2 (18 points). (a) Rank the following sets of compounds according to their increasing acidity. Place a 1 under the strongest acid, 2 under the next strongest, and so on. OH CH 3 OH O COOH OH (b) Rank the following sets of compounds according to their increasing acidity. Place a 1 under the strongest acid, 2 under the next strongest, and so on. O O O COOH CF 3 F 3 C F 3 C COOH O (c) Rank the following sets of compounds according to their increasing basicity or alkalinity. Place a 1 under the strongest base, 2 under the next strongest, and so on. N N H N H NH 2 NH 2
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Question 3 (32 points). Choose 8 of the 12 structures or names . Where a name is provided, write the structure of the compound. Where a structure is provided, write the name. Indicate clearly the answers you wish to have graded. OH (c) 2,4-dinitrophenol O O O O O O (d) 2-methylpentyl butanoate (i) cyclohexyl ethyl ether O N (g) 2,2-dimethylacetic propanoic anhydride (h) diisopropyl 2-methylmalonate N (a) (b) (e) (f) (j) 2-methyl-4-oxo-hex-5-enoyl chloride (k) (l) NH 2 COOH
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Question 4 (40 points). Choose 10 of the following 15 reactions , and complete the chemical equations by writing reactants, products or reagents in the appropriate
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This note was uploaded on 10/28/2010 for the course CHEM 235 taught by Professor Dr.poole during the Spring '10 term at Ball State.

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Final Exam 235 Spr 2004 - CHEM235 May 07, 2004 Final...

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