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Winter 2006 blank

Winter 2006 blank - Name Page1(W.06.215.E3.p1 I(23 points...

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Name:___________________ Page1 (W.06.215.E3.p1) O BnO OCH 3 OBn O Bn = CH 2 Ph O BnO OCH 3 OBn HO H 3 O + , H 2 O Three transformations are shown below. In each case, a Chem 215 student suggested a set of reaction conditions for carrying out these reactions. If you think the product that would form under these conditions is the one that is shown, please write "yes" in the answer space. If not, please draw the single major product that would be expected instead of the one shown. In cases where enantionmers, diastereomers, or anomers from, you only need to draw one of them. + H 3 N C CH 2 OH O OH + H 3 N C CH 2 OH O OCH 3 1 eq NaH 1 eq CH 3 I H O H H H H H OAc H OH OAc HO A c H H H H OH H CH 2 OAc 1) 2) H 3 O + (protonate) H (H 3 CH 2 C) 3 SiO N N N N NH 2 O OSi(CH 2 CH 3 ) 3 H H B. Complete the following transformation s. (JOC 2006 , 71 , 1009) (H 3 CH 2 C) 3 SiO N N N N HN O OSi(CH 2 CH 3 ) 3 H H O CH 3 CH 3 CH 3 I. (23 points) 4 5 5 5 + H 3 NC C CH O - O CH 3 H 3 C CH 3 OH HCl 4 H (i) (ii) (iii) Li (i) (ii) O Ph OH H H 1 eq
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Name:___________________ Page2 (W.06.215.E3.p2) The primary alcohol of α
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Winter 2006 blank - Name Page1(W.06.215.E3.p1 I(23 points...

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