Easy Reaction of ethoxybenzene with HBr?

What is the product formed when ethoxybenzene reacts with HBr?

Ethoxybenzene is Ph-O-C₂H₅. When it reacts with HBr, the products formed are phenol and ethyl bromide. The reaction and mechanism of the reaction of ethoxybenzene with HBr is as:

What is Substitution reaction?

The substitution reaction is defined as a reaction in which the functional group of one chemical compound is substituted by another group or it is a reaction which involves the replacement of one atom or a molecule of a compound with another atom or molecule. Here nucleophilic substitution reaction occurs. Bromide ion (Br^–) attacks on Ethyl group, so that phenol and ethyl bromide formed as the final products.

Explanation of mechanism involved

In first step of reaction mechanism, the lone pair of oxygen in ethoxybenzene attacks on H of HBr molecule, then Br^– leaves as leaving group.

Now a intermediate is formed with positive charge on oxygen atom. In given intermediate figure, two bonds are indicated as (a) and (b). Bond (a) has partial double bond character due to the resonance of lone pair of oxygen with the benzene ring, so its bond length become smaller than the pure single bond, so it is difficult to break. So, the bond (b) will break, then phenol and ethyl carbocation will form.

In the last step, the Br^– ion, which left out in first step, attacks on the ethyl carbocation to form ethyl bromide.

Hence, the products formed when ethoxybenzene reacts with HBr are phenol and ethyl bromide.

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