When the molecule 3-methylcyclohexene reacts with HCl, a rearrangement occurs, but when 3-methylcylohexene reacts with Cl2 with H2O as solvent, no rearrangement occurs.
a) Write the complete mechanism for the reaction of the above molecule with HCl. Used curved arrows to indicate the formation or breakage of covalent bonds, label all charges, and show each step separately.
b) Now write the complete mechanism for the reaction of the above molecule with Cl2 and H2O. In your structures, be sure to indicate clearly the stereochemistry for this reaction.