2011 DAT Destroyer #172 OCHEM

[pandalove89]

Ehtylmagnesium chloride C2H5MgCl would not react with which of the following?
a)methanol
b)diethyl ether
c)acetic acid
d)methylamine
e)propyne

Since it is a grignard reagent (base) the solution says that we are looking for a basic reactant because we don't want the grignard reagent to react with an acid.

So shouldn't it be d) ? I thought methylamine was a base. The answer is b).....which i thought was slightly acidic

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[frances362002]

More accurately it should be that we don't want the grignard reagent to react with any thing that has an acidic H (or in a more general sense, a dissociable H). Only ether has no acidic H. Although methylamine is slightly basic, its pKa is still lower than hydrocarbons. So its H is still dissociable when it's faced with organometallic reagent.

Ehtylmagnesium chloride C2H5MgCl would not react with which of the following?
a)methanol
b)diethyl ether
c)acetic acid
d)methylamine
e)propyne

Since it is a grignard reagent (base) the solution says that we are looking for a basic reactant because we don't want the grignard reagent to react with an acid.

So shouldn't it be d) ? I thought methylamine was a base. The answer is b).....which i thought was slightly acidic