C357_PPS_12_Solutions_2007 - C357 PPS#12 Solutions 1) left...

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C357 PPS#12 Solutions Page 1 of 3 1) left to right, top to bottom 6-bromo-4-(2’-propenyl)-1-cyclohexene 3,3-dibromo-1,4-cyclohexadiene (2Z, 7E) 8-bromo-2-chloro-5-methyl-2,7-undecadiene (3E, 5E) 1,3,5,7-octatetraene (1E) cyclodec-1-ene (1E, 3E) 2,3-dichloro-1,3-cyclopentadiene (2E) but-2-ene 6-bromo-4-(1’-cyclohexenyl)-1-cyclohexene 1,3,5,7-cyclooctatetraene (3E) 6,6,7,7,8,8,8-heptabromo-3-octene 2) Propose a reasonable mechanism to account for the following observed reaction. H 3 C CH 3 H H HC l H 3 C CH 3 H H H + Cl- H 3 C CH 3 H H H Cl 3) Propose a reasonable mechanism to account for the following observed reaction. H 3 C CH 3 H H l H 3 C CH 3 H H H + H 2 O H 3 C CH 3 H H H O + H H Cl- H 3 C CH 3 H H H OH
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Page 2 of 3 4) Propose a reasonable mechanism to account for the following observed reaction. H 3 C CH 3 H H BH H H H 3 C CH 3 H H BH 2 H NaOH/H 2 O H 2 O 2 H 3 C CH 3 H H OH H - OH H HOO HOO - H 3 C CH 3 H H B - H H H O O H B H H O H H H 3 C CH 3 H (boron rearrangement
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