Question

What alkyl halide or product will I get if I mix 2,4-dimethyl-3-pentanol with NaBr and sulfuric acid, and what substitution mechanism, SN1 or SN2 will that reaction undergo? Thanks in advance.

What if I mix 1-propanol with NaBr and sulfuric acid, what mechanism would that be?

What if I mix 2-pentanol with NaBr and sulfuric acid, what mechanism would that be?

Answer 1

You need to look at the stability of the + ion formed. There is a good description on the wikipedia pages:

http://en.wikipedia.org/wiki/SN2_reaction

http://en.wikipedia.org/wiki/SN1_reaction

Answer 2

for 1-propanol with NaBr and sulfuric acid, can I assume the mechanism is SN2 because the alcohol is on a primary carbon? I"m confused because when I write out the reaction, there will be a primary carbocation, and I'll have to do a shift right? I thought the product would be bromopropane but with the shift it will be 2-bromopropane?

for 2-pentanol, since the alcohol is on a secondary carbon, it can be either SN1 or SN2. I'm still confused