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Ch12B - Fall2010 CHEM222 Akira Kawamura Chapter 12B...

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Fall2010 CHEM222 Akira Kawamura Chapter 12B Alcohols from Carbonyl Compounds NOTE: Exam 4 is on Wed Dec 15 th (5:40-7:10 pm, 510N) A. Overview Today’s main goal: Grignard reaction and its application to organic synthesis Why important? Construction of carbon framework is the central challenge in organic synthesis. Grignard reaction is one of the key reactions used to assemble carbon fragments into a large framework. Key points: 1) Nucleophilic attack of carbanion to carbonyl (carbanion is a great nucleophile) 2) Preparation of carbanion nucleophiles 3) Use of Grignard reagents for primary ROH synthesis: 4) Restrictions: Carbanion is also a powerful base. They react with even a weakly acidic proton (-OH, etc.). B. Problem session 12.5-12.8 Problems 12.19b,c,e What is the major product of each of the following reactions? 12.5-12.8 Problem 12.22 Draw a stepwise mechanism of the following reaction. 12.5-12.8 Propose a synthesis of each of the target molecules (TMs) from the designated starting materials (SMs) and any necessary reagents.
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