222-08 Exam #2

222-08 Exam #2 - Name Place your name on the upper right...

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Place your name on the upper right corner of each succeeding page (By signing, I promise to abide by the Emory Honor Code)______________________________________________ Chemistry 222 Exam 2 March, 25 2008 The exam is budgeted for ~110 minutes, but you may have up to 150 minutes to finish it. Question values correspond to allotted time; don’t waste too much time on a cheap question. Good answers can fit in the space provided. Don’t waste time giving more information than the question asks for, but be sure to answer all of its parts. Now the medicine man comes and he shuffles inside He walks with a swagger and he says to the bride "Stop all this weeping, swallow your pride You will not die, it's not poison" Bob Dylan , Tombstone Blues , 1965 Name ____________________________________________ 1
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1. (3 points) What does LDA stand for? Draw its complete structure. 2. (8 points) Provide the appropriate chemical structure above each description. acetone glycerol benz y l bromide enamine 3. (8 points) Draw the complete arrow-formalism mechanism for the following conversion. Be sure to draw the correct structure of the final organic product. Your structure must be drawn in its most stable conformation . Old School: A simple “flat” drawing will not suffice. You must show shape/perspective of ring(s) as well as you possibly can. N CH 3 H 3 O + H 2 O O HO OH H + Name ____________________________________________ 2
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4. (24 points) Provide the major product (or missing reagents) for the following conversions. Be sure to indicate stereochemistry when necessary . O O CH 3 1. LiAlH 4 2. H 3 O + O H OH + (CH 3 ) 3 SiCl CH 3 O excess Br 2 , NaOH O CH 3 1. LDA 2. PhCH 2 Br H 3 C O OEt H 3 C O H CH 3 NH 2 , H + O CH 3 H 3 C O H 3 C 1. , H+ 2. EtBr N H H 3 O + H 2 O O O + CH 3 O NaOH, H 2 O MVK H 3 O + H 2 O N 2 H 4 , KOH, Δ Name ____________________________________________ 3
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5. (15 points) Provide the correct final product for the following three guided, synthetic problems. You may
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222-08 Exam #2 - Name Place your name on the upper right...

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