Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Video Lessons

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Problem: Draw both resonance structures of the most stable carbocation intermediate in the reaction(s) shown.You do not have to consider stereochemistry.Do not include anionic counter-ions, e.g., I-, in your answer.Draw one structure per sketcher. Add additional sketchers using the dropdown menu in the bottom right corner.Separate resonance structures using the ? symbol from the dropdown menu.

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For this problem, we have to draw the resonance structures of the most stable carbocation intermediate in the reaction below

  • These reactions will proceed to a conjugated hydrohalogenation which is known to produce multiple products
  • This will follow a simple hydrohalogenation mechanism except we have a possible conjugation which stabilizes the resonance structure
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Problem Details

Draw both resonance structures of the most stable carbocation intermediate in the reaction(s) shown.

You do not have to consider stereochemistry.

Do not include anionic counter-ions, e.g., I-, in your answer.

Draw one structure per sketcher. Add additional sketchers using the dropdown menu in the bottom right corner.

Separate resonance structures using the ? symbol from the dropdown menu.

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Based on our data, we think this problem is relevant for Professor Mullen's class at TAMU.