Why Can T-Butyl Chloride Undergo Substitution but Isopropyl Chloride Cannot?

[physics(L)10]

Homework Statement

T-butyl chloride can undergo substitution reaction to create C4H9OH, but isopropyl chloride cannot. Why is this?

Homework Equations

The Attempt at a Solution

I'm guessing it has to do with the extra carbon. Maybe since it is a secondary halide, the substitution takes the H off instead of the Cl?

 

[sjb-2812]

Homework Statement

T-butyl chloride can undergo substitution reaction to create C4H9OH, but isopropyl chloride cannot. Why is this?

Homework Equations

The Attempt at a Solution

I'm guessing it has to do with the extra carbon. Maybe since it is a secondary halide, the substitution takes the H off instead of the Cl?

Well, you can form 2-methylpropanol from IPA via things like metallation and addition of formaldehyde, but this is addition, not substitution. So the only thing that's relevant here is the number of carbons, in my opinion.

 

[chemisttree]

That's a trick question.