Multiple Choice
Why are two equivalents of elemental lithium needed to create an organolithium reagent, while only one equivalent of elemental magnesium is needed to create a Grignard reagent?
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13. Alcohols and Carbonyl Compounds
Preparation of Organometallics
Multiple Choice
Why must polar protic solvent NOT be used in reactions of Grignard and organolithium reagents?
A
The reagents are strong bases and will be quenched by polar protic solvents.
B
The boiling point of polar protic solvents are too low for the minimum required reaction temperature.
C
This statement is backward. Polar protic solvents MUST be used with Grignard and organolithium reagents.
D
The reagents are not soluble and will not dissolve in polar protic solvents.
Verified step by step guidance1
Understand the nature of Grignard and organolithium reagents: These reagents are highly reactive and function as strong bases and nucleophiles.
Recognize the characteristics of polar protic solvents: These solvents have hydrogen atoms bonded to electronegative atoms like oxygen or nitrogen, making them capable of hydrogen bonding.
Consider the interaction between Grignard/organolithium reagents and polar protic solvents: The hydrogen in polar protic solvents can react with the strong base nature of these reagents, leading to their quenching.
Analyze the solubility aspect: Grignard and organolithium reagents are typically not soluble in polar protic solvents due to their ionic nature and the solvent's hydrogen bonding network.
Conclude why polar protic solvents are unsuitable: The reactivity of Grignard and organolithium reagents with the hydrogen in polar protic solvents leads to their deactivation, making these solvents inappropriate for such reactions.
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