What are the products of the reaction of 1-methoxycyclohexene with dilute hydrochloric acid? 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?
Vinyl ethers are "masked" carbonyls, therefore in acidic aqueous environment the following pathway takes place: alkene protonation assisted by the methoxy group followed by nucleophilic attack of water with hemiacetal formation. Subsequent intramolecular proton transfer to the methoxy group makes it a good leaving group and cyclohexanone (the product) is formed while methanol is released.