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K E Y Please write the first three letters of your last name in the above boxes Organic Chemistry CH 310M/318M Dr. Jonathan L. Sessler EXAM 3 Thursday, December 04, 2008 Name:_______________________________ UT EID:_____________________________ Signature:____________________________ NOTE: The exam must be taken using blue or black ink to be eligible for a regrade in the case you have concerns regarding grading errors.
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1. Fill in the boxes with, as appropriate, either the reactants or organic products associated with the following transformations. (30 points) 2 N O O Br CCl 4 O Hg(II), H 2 SO 4 ,H 2 O Cl HCl 2 equiv. NaNH 2 1. B 2 H 6 2. H 2 O 2 /NaOH +B r 2 (cat.) HBr, peroxides CCl 4 THF DMF DMF THF Br Br Cl OH O H Cl
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2. Fill in the boxes with the appropriate reagents and experimental conditions or products to complete the following transformations (modified from Brown, Foote, Iverson, and Anslyn , Problem 7.21). (24 points) 3
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3. Using curved arrows to show flow of electrons, provide the complete mechanism for the transformation of 2,3-dimethylbutane-2,3-diol to 3,3-dimethylbutane-2-one shown below. Be sure to include all lone pairs and charges for intermediates and products. (20 points) 4
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4.
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This note was uploaded on 10/14/2009 for the course M 408d taught by Professor Sadler during the Spring '07 term at University of Texas.

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