Question

What is the product for the hydrochlorination of 1-nitrocyclohexene?

Answer 1

I predict that the product will be 1-chloro-2-nitrocyclohexane.

Explanation:

We would expect `"HCl"` to add to 1-nitrocyclohexene according to Markovnikov's rule and form 1-chloro-1-nitrocyclohexane:

However, this mechanism puts a positive charge on the carbon atom next to another positive atom:

In this case, the addition is more likely to be anti-Markovnikov.

This avoids two adjacent + charges in the intermediate and forms a secondary carbocation.

I predict the product will be 1-chloro-2-nitrocyclohexane.