[scienceguy]

Would hydroxide react with dichloromethane in a substitution reaction (SN2)? Or would the second chlorine cause too much steric hindrance?

[discodermolide]

Would hydroxide react with dichloromethane in a substitution reaction (SN2)? Or would the second chlorine cause too much steric hindrance?

Probably not. You would end up generating a carbene if the hydroxide was strong enough.

[scienceguy]

What about protonated isopropyl alcohol undergoing a substitution reaction (SN2) with 2,2-dichloropropane? Would there be too much steric hindrance there?

[discodermolide]

What about protonated isopropyl alcohol undergoing a substitution reaction (SN2) with 2,2-dichloropropane? Would there be too much steric hindrance there?

Do you mean de-protonated?
If so yes, there would be too much steric interference as the nucleophile must attack from the rear. Make a model.

[scienceguy]

Yes, I meant deprotonated. Thanks for the responses.

[orgopete]

Are you asking for the product of a reaction of 2,2-dichloropropane with isopropoxide?