Week_7.3_PurpleBook_Answers

Week_7.3_PurpleBook_Answers - 185 More Mechanisms and FMO...

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1. Consider the following interesting transformation: More Mechanisms and FMO Analysis OEt O + MgBr carbocation intermediate H + a) Provide a curved-arrow mechanism for the formation of the carbocation intermediate. b) The carbocation intermediate has a conjugated π -system .D rawt heHOMOo fth i s π -system and determine whether this thermal cyclization reaction is conrotatory or disrotatory. (circle one) CON DIS c) Provide a curved-arrow mechanism for the reaction of the carbocation intermediate to form the product. EtO O O MgBr O H + H 2 O HOMO (5 p orbitals, 4 e
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O H 3 C H H O CO 2 Me H O O O O H 3 C H H O Putting It Together: Diels-Alder Synthesis CO 2 Me 1. Propose syntheses of the following desired products from acyclic starting materials. A Diels-Alder reaction will be a key step in each synthesis. Be sure to account for stereochemistry where indicated! CO 2 Me (hint: think aldol) + O H Diels-Alder H 2 Pd CO 2 Me + H O Diels-Alder 1. O 3 2. Me 2 S (aldol condens.) O OH OH NaOMe H + Week 7 186
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1. 2. 1. 2. 2. Putting It Together: Reagents 1. Each of the following transformations can be carried out in one to two steps. Fill in the reagents and/or conditions required for each step. Be sure to consider the stereochemistry of each reaction! 1. 1. O O H 2. (plus enantiomer, as a racemic mixture) 1. 2. h ν (UV light) O heat OH O CN CN O NC CN heat (plus enantiomer, as a racemic mixture) heat D D D H D H h ν Week 7 187
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1. Fill in each box with a reactant that would provide the product indicated by the transformation. Be sure to indicate stereochemistry if it is relevant! (There may be more than one correct answer in some cases.) heat must be trans, but either enantiomer is OK. heat
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Week_7.3_PurpleBook_Answers - 185 More Mechanisms and FMO...

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