HBr
Strategy: Identify the type of reaction that will occur. Determine the regiochemistry of the addition reaction. Analyze the carbocation formed and determine whether a rearrangement will occur. If so, rearrange to form a more stable carbocation and complete the nucleophilic addition.
Step 6: The last step of the hydrohalogenation reaction is the addition of the bromide ion to the carbocation. Draw the product with non-bonding electrons, where applicable.