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Organic Chemistry, 6 th edition Paula Yurkanis Bruice Chapter 11 Organometallic Compounds Brian L. Groh Minnesota State University, Mankato Mankato, MN.

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Presentation on theme: "Organic Chemistry, 6 th edition Paula Yurkanis Bruice Chapter 11 Organometallic Compounds Brian L. Groh Minnesota State University, Mankato Mankato, MN."— Presentation transcript:

1 Organic Chemistry, 6 th edition Paula Yurkanis Bruice Chapter 11 Organometallic Compounds Brian L. Groh Minnesota State University, Mankato Mankato, MN Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

2 Which of the following solvents is (are) suitable for the preparation of a Grignard reagent? 11.1 A.Hexane B.Tetrahydrofuran C.Ethanol D.Ethyl ether E.B and D Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

3 Which of the following solvents is (are) suitable for the preparation of a Grignard reagent? 11.1 A.Hexane B.Tetrahydrofuran C.Ethanol D.Ethyl ether E.B and D Preparation of a Grignard reagent requires a polar, aprotic, coordinating solvent such as an ether. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

4 What is the product of the following reaction? 11.2 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

5 What is the product of the following reaction? 11.2 The Grignard reagent (nucleophile; R-MgBr or “C”) forms first which then reacts with a proton from H 2 O (electrophile). This is formally a reduction. THF is only a solvent. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

6 What is the major product of this reaction? 11.2 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

7 What is the major product of this reaction? 11.2 Nucleophilic ring opening of epoxides occurs at the least hindered carbon. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

8 The following reaction is an example of a ________ reaction A.Gillman B.Grignard C.Heck D.Stille E.Suzuki Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

9 The following reaction is an example of a ________ reaction A.Gillman B.Grignard C.Heck D.Stille E.Suzuki The Suzuki reaction is based upon reaction of organoborane compounds with alkenyl and aryl electrophiles. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

10 What type of reaction could not be used to accomplish the following: 11.5 A.Gillman ((CH 2 =CH) 2 CuLi) B.Grignard (CH 2 =CHMgBr) C.Heck (CH 2 =CH 2 ) D.Suzuki (CH 2 =CHB(OR) 2 ) E.All of these will work Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

11 What type of reaction could not be used to accomplish the following: 11.5 A.Gillman ((CH 2 =CH) 2 CuLi) B.Grignard (CH 2 =CHMgBr) C.Heck (CH 2 =CH 2 ) D.Suzuki (CH 2 =CHB(OR) 2 ) E.All of these will work The Grignard reagent would react with the carbonyl group, not the halide. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

12 Name the following reaction type: 11.6 A.Gillman B.Grignard C.Heck D.Suzuki E.Grubbs/metathesis Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

13 Name the following reaction type: 11.6 A.Gillman B.Grignard C.Heck D.Suzuki E.Grubbs/metathesis Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. The loss of an alkene to form the product is indicative of metathesis. + CH 2 =CH 2


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