bromide is a better nucleophile toward the intermediate bromonium ion than ethanol. what product would be obtained if ethanol did carry out this nucleophilic attack?
yes ma'am
To determine the product obtained when ethanol carries out a nucleophilic attack on the intermediate bromonium ion, we first need to understand the reactivity of bromide and ethanol as nucleophiles.
Bromide (Br-) is a better nucleophile than ethanol (CH3CH2OH) due to the difference in electronegativities between the halogen (bromine) and oxygen atoms. Bromine is much less electronegative than oxygen, meaning that the partial positive charge on the bromonium ion is less shielded than on the ethonium ion.
When an alcohol like ethanol acts as a nucleophile towards a bromonium ion, it will typically attack the less hindered carbon atom (the one with more atoms attached to it) in an SN2 (bimolecular nucleophilic substitution) reaction.
In the case of ethanol attacking the bromonium ion, it will most likely attack one of the carbon atoms of the bromonium ion, breaking the C-Br bond and forming a new C-O bond. As a result, the bromine atom will be replaced with an oxygen atom from ethanol, and the overall product will be an ether.
The specific product will depend on which carbon atom of the bromonium ion the ethanol attacks. If ethanol attacks the carbon atom that is directly bonded to the bromine, it will form ethyl bromide (CH3CH2Br) as the product. On the other hand, if ethanol attacks the other carbon atom of the bromonium ion, it will form tert-butyl bromide (CH3C(CH3)2Br) as the product.
So, the product obtained when ethanol carries out a nucleophilic attack on the bromonium ion depends on the specific regioselectivity and stereochemistry of the reaction.