1) I add the proton to the C1-C2 double bond: I obtain a tertiary allylic carbocation and a secondary carbocation.
2) I add the proton to the C3-C4 double bond: I obtain a secondary carbocation and a secondary allylic carbocation.
3) The chloride ion bonds to the tertiary allylic carbocations stabilized by resonance from point 1: I obtain 3-chloro-3-methylcyclohexene and 3-chloro-1-methylcyclohexene.
These are the 1,2- and 1,4-addition products (can someone help me understand how I can distinguish them in this way?).
4) The chloride ion bonds to the secondary allylic carbocations stabilized by resonance from point 2: I obtain 6-chloro-1-methylcyclohexene (Is this the correct IUPAC name?). What type of products are these? 1,2 or 1,4?
I was also asked which of the four products are formed in the greatest quantity and why. I believe that 3-chloro-3-methylcyclohexene and 3-chloro-1-methylcyclohexene are formed in the greatest quantity because they are produced through the most stable intermediates. Am I correct? Do the other products not form at all, or do they form in larger quantities?
I really appreciate all the responses, they were very helpful! Thanks for your support!