Addition of Halogen Acids to Alkenes
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry of the reaction and the possibility of carbocation rearrangement.Click the mouse on the reactant molecule to view the answer;
click on the reagent to review the mechanism and regiochemistry of the reaction.
The addition of HCl to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl chloride with the chlorine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed. In this reaction, the tertiary carbocation is preferentially formed.
The addition of HBr to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl bromide with the bromine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed. In this reaction, the tertiary carbocation is preferentially formed.
The addition of HBr to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl bromide with the bromine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed. In this reaction, the initially formed secondary carbocation undergoes a 1,2-methyl shift to give the tertiary carbocation, which adds the bromide anion.
The addition of HCl to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl chloride with the chlorine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed. In this reaction, the tertiary carbocation is preferentially formed.
The addition of HCl to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl chloride with the chlorine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed.
The addition of HBr to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl bromide with the bromine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed.
The addition of HBr to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl bromide with the bromine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed.
The addition of HCl to an alkene proceeds through a carbocation intermediate and results in the formation of an alkyl chloride with the chlorine bonded to the alkene carbon which would form the most stable carbocation (Markovnikov addition). Rearrangements are commonly observed.