(Solved) HBr relative reaction rates (organic chemistry)?

Hello,
I need help with a question from my assignment. I understand HBr reaction can go via either Sn1 or Sn2, and I also understand Sn1 favors highly substituted and Sn2 the opposite. But what about the effect of substitution that's not on the double bond (like somewhere "far" away on the chain)? Also, if you have a methyl alcohol and a tertiary alcohol reacting with HBr, which one's faster? I can't tell which one is faster because the first favors Sn2 and the second favors Sn1.

Here's the question: Select the fastest and slowest in each Group- in the reaction that converts each species to the corresponding alkyl bromide on being treated with HBr.

Group I:
a. 1-hexanol
b. 2-hexanol
c. 2-methyl-2-hexanol
d. 4-methyl-2-hexanol
e. 4,4-dimethyl-2-hexanol

Group II:
a. 2-cyclohexyl-1-propanol
b. 1-cyclohexylethanol
c. 2-methylcyclohexanol
d. cyclohexanol
e. 1-methylcyclohexanol

Thank you very much! If you could explain why as well as answer this question that'd be great! I want to understand it.

Lily
Also, say you have 1-hexanol and 1-butanol reacting with HBr via Sn2. Which one's faster? Does the chain length matter?

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HBr relative reaction rates (organic chemistry)?

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