organometallic nucleophiles

Question 1

components to make organometallic nucleophiles

Answer 1

• highly oxidizable metal (Mg, Li, Na)
• reducible organohalide (often R-Br)

Question 2

charges when making organometallic nucleophiles

Answer 2

• starts with partial + for R carbon and partial - for Br
• ends with partial - for R carbon and partial + for metal

Question 3

rules for running the reaction to make organometallic nucleophiles

Answer 3

• aprotic solvent
• Argon gas (no air)
• cool temperature to slow reaction

*all of these are because the base (C-) is so strong!

Question 4

why can’t organometallic nucleophiles be with protic solvents

Answer 4

• R group is essentially a carbanion, which is a very strong base
• reacts as a base with protic solvents and reagent is destroyed

Question 5

Grignard reagents

Answer 5

• organomagnesium nucleophile

Question 6

other ways to make organometallic compounds

Answer 6

• more basic organometallics can act as catalyst (??)

Question 7

when can organometallic compounds react with carbonyls

Answer 7

• react as nucleophiles with aldehydes and ketones (not carboxylic acids or amides because of H!)

Question 8

Grignard reactions with esters

Answer 8

• 2 mol Grignard reagent reacts for every 1 mol ester!
• reacts 2x to form a tertiary alcohol