1. Organic Chemistry, 6th 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. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
11.1
Which of the following solvents is (are) suitable for the preparation of a Grignard reagent?
Hexane
Tetrahydrofuran
Ethanol
Ethyl ether
B and D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

3. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
11.1
Which of the following solvents is (are) suitable for the preparation of a Grignard reagent?
Hexane
Tetrahydrofuran
Ethanol
Ethyl ether
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
What is the product of the following reaction?
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

5. What is the product of the following reaction?
11.2
What is the product of the following reaction?
The Grignard reagent (nucleophile; R-MgBr or “C”) forms first which then reacts with a proton from H2O (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
What is the major product of this reaction?
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

7. What is the major product of this reaction?
11.2
What is the major product of this reaction?
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.
11.5
The following reaction is an example of a ________ reaction.
Gillman
Grignard
Heck
Stille
Suzuki
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

9. The following reaction is an example of a ________ reaction.
11.5
The following reaction is an example of a ________ reaction.
Gillman
Grignard
Heck
Stille
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
What type of reaction could not be used to accomplish the following:
Gillman ((CH2=CH)2CuLi)
Grignard (CH2=CHMgBr)
Heck (CH2=CH2)
Suzuki (CH2=CHB(OR)2)
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
What type of reaction could not be used to accomplish the following:
Gillman ((CH2=CH)2CuLi)
Grignard (CH2=CHMgBr)
Heck (CH2=CH2)
Suzuki (CH2=CHB(OR)2)
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
Name the following reaction type:
Gillman
Grignard
Heck
Suzuki
Grubbs/metathesis
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

13. Name the following reaction type:
11.6
Name the following reaction type:
+ CH2=CH2
Gillman
Grignard
Heck
Suzuki
Grubbs/metathesis
The loss of an alkene to form the product is indicative of metathesis.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.