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ago in Organic Chemistry by (550 points)
What is the mechanism of the reaction between ethanol and HBr? Draw the complete mechanism, including any intermediates formed during the process. Be sure to explain the key steps involved in the reaction and the overall reaction mechanism.

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ago by (630 points)
As a text-based AI, I cannot draw the mechanism, but I can describe it for you. The reaction between ethanol  CH3CH2OH  and HBr  hydrogen bromide  is an acid-catalyzed substitution reaction, specifically an SN1 reaction. The overall reaction is:CH3CH2OH + HBr  CH3CH2Br + H2OHere's the step-by-step mechanism:1. Protonation of the alcohol: The lone pair of electrons on the oxygen atom of the ethanol molecule attacks the hydrogen atom of the HBr molecule. This results in the formation of a protonated alcohol  CH3CH2OH2+  and a bromide ion  Br- .CH3CH2OH + HBr  CH3CH2OH2+ + Br-2. Formation of the carbocation: The protonated alcohol molecule undergoes heterolysis, where the bond between the oxygen and the carbon atom breaks, and both electrons go to the oxygen atom. This results in the formation of a water molecule  H2O  and a carbocation intermediate  CH3CH2+ .CH3CH2OH2+  CH3CH2+ + H2O3. Nucleophilic attack: The bromide ion  Br-  acts as a nucleophile and attacks the carbocation  CH3CH2+ , forming a new bond between the carbon and the bromine atom. This results in the formation of the final product, bromoethane  CH3CH2Br .CH3CH2+ + Br-  CH3CH2BrThe overall mechanism involves the initial protonation of the alcohol, followed by the formation of a carbocation intermediate and the nucleophilic attack by the bromide ion. The final products are bromoethane and water.
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