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Question

CH3CH2OH react with CH3MgBr product is....... Please please show the reaction mechanism....

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Solution

Let us start with the basics. What are Grignard reagents? They are a group of reagents, which are generated by reacting organic halides and magnesium metal (Mg) mostly in the vicinity of ether. They have general formula RXMgX. R denotes an organic group (alkyl or alkenyl) while X represents a halogen. They are applied in Grignard reaction.

Grignard reagents are good nucleophiles. Thus, they react with electrophiles like epoxides and carbonyl compounds. In addition, they are strong bases. Hence, they react with acidic hydrogens.

The reaction between ethanol and Grignard reagents is an acid-base reaction, but not a nucleophile-electrophile reaction. Ethanol has an acidic hydrogen (acidic proton). Even though is not stronger acid, it is capable of protonating Grignard reagents as shown below:

CH3CH2OH + R’MgX ———} CH3CH2O-(MgX)+ + R’-H

NB: A compound with an acidic hydrogen is more acidic as compared to hydrogen of alkanes or alkenes.


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