Week_6.3_PurpleBook_Answers

Week_6.3_PurpleBook_Answers - 153 Conjugate Additions:...

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Conjugate Additions: Retrosynthesis 1. Each of the following products can be synthesized via a conjugate addition. Suggest appropriate starting materials to use in each case. a) b) c) O CH 3 NO 2 O 2 N O EtO O Ph O Ph + NaOR or NaH + NaOEt + O OEt O N O OH O NH 2 OH Week 6 153
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Conjugate Additions: Mechanisms 1. Provide a complete curved-arrow mechanism for all steps in the following multi-step transformation. O H O 1. Me 2 CuLi 2. H 3 O + workup O "Me - " O H O O O HO H 2 O OH +H + OH H OH 2 + 2 -H + Week 6 154
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Robinson Annulation: Retrosynthesis 1. Give the structures of the organic compounds required to prepare each of the following cyclic ketones using the Robinson Annulation for the key bond forming steps. a) b) c) O O + O O CO 2 Me + MeO 2 C O 2 Me Ph Ph O + Ph O 2 Et O OEt O EtO 2 C 2 Et OO OMe Week 6 155
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O O OEt O O O EtO H O OEt O O O OEt O O O EtO O O O OEt HO H O O OEt HO + NaOEt EtOH Robinson Annulation: Mechanism 1. The Robinson annulation can be used to produce a six-membered ring. Show the product formed when the following two molecules are reacted with a base: :OEt :OEt H + transfer Provide a curved-arrow mechanism for the transformation you indicated above: O O OEt O O OEt O H + NaOEt EtOH Week 6 156
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O CuLi Ph Br
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_6.3_PurpleBook_Answers - 153 Conjugate Additions:...

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