The reaction generates carbocations, which are much less stable in non-polar solvents like CCl4. The best solvent for a carbocation rearrangement is a highly polar, ionizing solvent.

The group that is migrating remains on the same face. This is OK because the carbocation has an empty p orbital and in theory can be attacked from either face.

Glad you found it useful Kathy!

Cyclopropane is a very, very interesting case. Carbocations on an alkyl group adjacent to a cyclopropane are particularly stable. The result is not ring expansion, but a non-classical carbocation called the cyclopropylcarbinyl cation: https://en.wikipedia.org/wiki/Carbocation#Specific_carbocations

Actually the carbon attached to Cl will become the carbocation. Cl has a pair of electrons which can stabilize adjacent carbocations via pi donation. See this post https://www.masterorganicchemistry.com/2018/03/05/why-are-halogens-ortho-para-directors/

While HCl will give you 2-chloropropane, KOH will perform elimination (E2) to give you back propene.
But why not just add H3O+ (H2SO4 / H2O) and cut out the middleman? Or oxymercuration?

Love your post, thankyou