Chapter 9: Using organometallics to make C-C bonds

Question 1

How can you make Grignard reagents

Answer 1

Grignard reagents are made by reacting magnesium turnings with alkyl halides in ether solvents to form solutions of alkylmagnesium halide. Iodides, bromides, and chlorides can be used, as can both aryl and alkyl halides.

Question 2

Name 4 common solvents to make Grignards in

Answer 2

1. Ether
2. Tetrahydrofuran
3. dioxane
4. dimethoxymethane

Question 3

What is the name of the process used to make Grignards

Answer 3

Oxidative insertion or oxidative addition

Question 4

Why must organometallics be kept away from water?

Answer 4

react very rapidly and highly exothermically with water to produce alkanes. Anything that can protonate them will do the same thing. Very difficult to remove the proton after protonation

Question 5

What is transmetallation

Answer 5

a chemical process where a ligand bound to a metal ion is exchanged with another metal ion in solution. This exchange typically occurs when a new metal ion has a higher affinity for the ligand than the original metal ion.

Question 6

What are the 5 ways to make organometallics?

Answer 6

1. oxidative insertion of mg into alkyl halides
2. oxidative insertion of li into alkyl halides
3. deprotonation of alkynes
4. halogen-metal exchange
5. transmetallation

Question 7

How does carbon dioxide react with organometallics to form carboxylates?

Answer 7

1. Form the organometallic
2. reaction with electrophile (co2)
3. acid work up