14C_syn_exs_&_strategies

14C_syn_exs_&_strategies - 14 C synthesis strategies,...

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14 C synthesis strategies, Chem 315/316 / Beauchamp 1 Use clues in the target molecule to determine what the last step could have been. Once you work back one step, use clues in that molecule to determine how you could work back one additional step. Repeat this process until you get to the necessary starting conditions, i.e. allowable 14 C starting units (*CH 4 , *CO 2 , Na*CN where “*” indicates a radioactive 14 C isotope). Until aromatic chemistry is covered bromobenzene is also available. Starting Structures: CH 4 Br Examples – Target Molecules (TM - #) Straight chain C5 alcohols OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH * * * * * * * * * * * * * 1 2 3 4 56 78 9 10 11 12 13 14 15 16 OH * CH 2 O Br * Br CH 2 O * HO O Br HO CH 2 O Br TM - 1 CH 2 O Br * CH 2 O * TM - 2 OH * Br CH 2 O * Br * CH 2 O * O TM - 3 OH * Br CH 2 O * C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\316\C14 Syn Problems\14C_syn_exs_&_strategies.doc
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14 C synthesis strategies, Chem 315/316 / Beauchamp 2 Br * CH 2 O * O TM - 4 OH * Br CH 2 O * * HO CH 3 Br HO * Br * O TM - 5 OH * HO * O CH 3 Br * * CH 3 Br * O Br O TM - 6 OH O TM - 7 OH * CH 3 Br * O H OH O Br O Br TM - 8 OH * * O H Br * OH CH 3 Br CH 2 O * OH * CH 3 Br O H * * OH CH 2 O * Br OH * O * Br * * OH C O H O R CH 3 Br 2 eqs. * Br TM - 9 OH * O H Br CH 2 O * * * HO C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\316\C14 Syn Problems\14C_syn_exs_&_strategies.doc
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14 C synthesis strategies, Chem 315/316 / Beauchamp 3 TM - 10 OH * Br CH 2 O * O * * HO CH 3 Br TM - 11 OH * Br CH 2 O * O * * HO CH 3 Br TM - 12 OH Br O O TM - 13 Br OH * O CH 3 Br * OH * O H * Br HO * OH (above, TM-11) (above, TM-13) TM - 14 OH O H * Br * * OH (above, TM-10) TM - 15 OH O O H R * Br * 2 eqs. O O H H R Br * TM - 16 OH O O H R Br 2 eqs. O H Br O O H H R Br C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\316\C14 Syn Problems\14C_syn_exs_&_strategies.doc
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14 C synthesis strategies, Chem 315/316 / Beauchamp 4 Examples – Target Molecules (TM - #) 4C chain with methyl branch alcohols OH OH OH OH OH OH * * * * * * 1 2 3 4 56 7 8 9 10 11 13 14 15 16 * OH * OH * OH * OH OH OH OH OH OH OH * * * 12 * 17 OH 18 OH 19 OH 20 OH 21 OH * * * TM-1 OH * CH 2 O * Br HO HO HO O H Br O H CH 3 Br O CH 3 Br TM-2 OH * CH 2 O * Br HO O H Br CH 3 Br * * CH 2 O HO * * TM-3 OH * CH 2 O * Br HO CH 3 Br * O H * C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\316\C14 Syn Problems\14C_syn_exs_&_strategies.doc
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14 C synthesis strategies, Chem 315/316 / Beauchamp 5 TM-4 OH * CH 2 O * Br HO O H Br CH 3 Br * * CH 2 O HO * * TM-5 OH * CH 2 O * Br HO CH 3 Br * * O TM-6 OH CH 2 O Br HO CH 3 Br O O H Br O H TM-7 O Br CH 3 Br * * OH HO (above, TM-6) CH 3 Br * OH O * OH * O H CH 3 Br * TM-8 Br * OH O * OH * O H O CH 3 Br * R O H O * H R Br TM-10 O * OH CH 3 Br * OH O CH 3 Br C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\316\C14 Syn Problems\14C_syn_exs_&_strategies.doc
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14 C synthesis strategies, Chem 315/316 / Beauchamp 6 OH TM-11 O Br * OH TM-12 O CH 3 Br * CH 3 Br * OH Br O H * OH * CH 3 Br * O H OH * TM-13 Br O H * O H O R * CH 3 Br 2 eqs.
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14C_syn_exs_&_strategies - 14 C synthesis strategies,...

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