When 1-methoxycyclohexene is treated with dilute aqueous hydrochloric acid, methanol is produced along with another organic product. Identify this product. Explain why methoxycyclohexane is inert under these reaction conditions.
I don't understand why it isn't just a simple addition to the double bond. I get that there's conjugation but is this what makes things different? I don't get why methanol is the leaving group and therefore I cannot predict the other product. Also, it says that methoxycyclohexane (the same molecule without the double bond) is inert under these conditions. Why does it not undergo substitution? The oxygen could surely be protonated and then methanol would be a good leaving group which would give rise to substitution (probably SN1). Why is this not the case?