chpt-7-8-synthesis.deuterium_ans

chpt-7-8-synthesis.deuterium_ans - major alkene can be...

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OH (a) D (b) OH OH D mixture of stereoisomers (c) OH D Br + enantiomer (d) OH OCH 3 D mixture of stereoisomers H 2 SO 4 Δ 1) 9-BBN-d 2) CH 3 CH 2 CO 2 H H 2 SO 4 Δ H 2 SO 4 Δ H 2 SO 4 Δ 1) Hg(OAc) 2 , CH 3 OH 2) NaBD 4 1) Hg(OAc) 2 , H 2 O 2) NaBD 4 1) 9-BBN-d 2)Br 2 - OCH 3 Deuterium Sources: 9-BBN-d CH 3 CH 2 C D 2 NaBD 4 D 2 O O OD The following synthetic transformations involve introduction of deuterium into a compound. Using the deuterium sources listed below, show how the following transformations could be conducted. You can use any non- deuterated reagents as needed. Assume, with reactions that form alkene mixtures, that the
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Unformatted text preview: major alkene can be separated and used in subsequent reactions. Also, in synthesis problems, it is expected that one show all intermediate compunds, not mechanistic intermediates, but the result of each synthetic step. CD 2 I 2 (e) OH OD Br (g) OH CH 3 CH 2 CHCHCH 3 D D R,R- and S,S-isomers only H 2 SO 4 H 2 SO 4 C C H CH 3 CH 2 CH 3 H C C D D CH 3 CH 2 H H CH 3 C C D D H CH 3 H CH 3 CH 2 D 2 Pt Br 2 D 2 O (f) OH D D H 2 SO 4 CD 2 I 2 Zn (Cu) + enantiomer...
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chpt-7-8-synthesis.deuterium_ans - major alkene can be...

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