Ochem3 - 1 Your name Your 10 # YourTA . . . Chemistry 10BA...

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1 Your name . Your 10 # . YourTA . Chemistry 10BA -:r:;'11 Q I eX~ Final exam pracic.e- fest 1 July 23 wiker Problem score 1 30 points 2 10 points 3 6 points 4 11 points 5 tc eotnts 6 to oomts 7 17 ooints B tz ootnts 9 8 points 10 16 points Total 130 points
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2. Problem 1 (30 points) Complete the following reactions where the starting materials, the reagents and/or the products are missing as indicated by empty boxes. HNOs CHs 0-0-80s H AICIs CfI ~CI-< o a compound wtth 10 C OH ~Br CIA.;! C~,Fe ~ C:=CH __ .. .. CI
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3 See", +h ,.$ re <1 cLio (l -H-, is. 'tuartq( '------------ Problem 2 (10 points) Consider the tosylate of 3-phenyl-2-butanol: OTos Ph The stereoisomer (2S,3S)-3-phenyl-2-butanol undergoes E2 elimination on treatment with a strong base to yield 2-phenyl-2-butene. a) Draw a Newman projection of the starting material and show the arrow-pushing mechanism for the elimination reaction. b) Write the structure of the product alkene and determine whether it is E or Z.
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Problem 3 (6 points) Draw all the important resonance forms of the following compounds and in each case predict where the compound would undergo an electrophilic substitution reaction. a) benzaldehyde b) bromobenzene Problem 4 (1 1 points) Consider the following molecules. Circle the aromatic ones, box the antiaromatic ones, and leave the rest untouched. ·r.r"~N· 'N):~i '·0' I!. ~ '0 II A ) () D ::::. .. N N N .. I CH 3 0 0 C 0 oCH3
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5 (10 points) How would you prepare the following compound using an alkyl halide and an alkyne as starting materials? More than one step is needed. Show the reactions. Do not show mechanisms. H
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This note was uploaded on 08/09/2008 for the course CHEM 108A taught by Professor Bernasconi during the Spring '07 term at University of California, Santa Cruz.

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Ochem3 - 1 Your name Your 10 # YourTA . . . Chemistry 10BA...

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