Question

Organic Chemistry Predict the product(s)? Could someone help? What did I do wrong???

Answer 1

I predict the main product to be 1-chloro-1-ethenylcyclohexane.

Explanation:

The `"HCl"` will protonate both ends of the butadiene system.

If it protonates the end of the side-chain, we get a resonance-stabilized carbocation:

Each of the resonance contributors is a secondary carbocation.

If the `"HCl"` protonates the ring, we again get a resonance-stabilized carbocation:

In this case, one of the contributors is a stable tertiary carbocation and the other is an unstable primary carbocation.

The major product will result from the attack of chloride ion at the tertiary carbocation.

I predict the major product to be 1-chloro-1-ethenylcyclohexane.

Three other chlorides are formed in small amounts.