Why is ether used as the solvent during Grignard reactions?

Answer 1

Ether is used as a solvent because it is aprotic and can solvate the magnesium ion.

A Grignard reaction involves the reaction of an alkyl (or aryl halide) with magnesium metal to form an alkylmagnesium halide.

#"R-X" + "Mg" stackrelcolor(blue)("dry ether"color(white)(X))(→) "R-MgX"#

Diethyl ether is an especially good solvent for the formation of Grignard reagents for two reasons.

(a) Ether is an aprotic solvent

The #"R-Mg"# bond is highly polar: #stackrelcolor(blue)(δ^(-))("R"color(white)(l))-stackrelcolor (blue)(δ^+)("Mg")"X"#

The Grignard carbon is highly basic and reacts with the acidic protons of polar solvents like water to form an alkane.

#stackrelcolor (blue)(δ^(-))("R"color(white)(l))"-"stackrelcolor (blue)(δ^+)("Mg")"X" + "H-OH" → "R-H" + "HO-MgX"#

Ether has no acidic protons, so Grignard reagents are stable in ether.

(b) Ether is a great solvating agent

The #"MgX"# bond in a Grignard reagent is ionic: #"R-Mg"^+ color(white)(l)"X"^-#.

Hence, it is difficult to form a Grignard reagent in a nonpolar solvent.

The #"C-O"# bond in an ether is quite polar, and the oxygen of the dipole can solvate and stabilize the #"R-Mg"^+# ion.

Thus, Grignard reagents are soluble in ether.

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Answer 2

the very simple reason is that in ether, there is no acidic Hydrogen present on which the Grignard reagent #RMgX# can attack and get itself converted to #R-H#.

thus to prevent Grignard from decomposing simply to an alkane/ene/yne, we use ether.

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Answer 3

Ether is commonly used as the solvent during Grignard reactions because it is non-reactive with Grignard reagents, it stabilizes the reactive intermediates formed, and it helps solubilize the organic reactants and products. Additionally, ether is relatively inert towards the reagents involved in the Grignard reaction, allowing for efficient reaction conditions and high yields of the desired products.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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