Can primary, secondary, and tertiary alcohols undergo halogenation?

Question

We did a lab and we had to predict whether
1-butanol (primary) , 2-butanol (secondary), and 2-methyl-2-propanol (tertiary) undergo halogenation. We mixed those 3 alcohols with concentrated HCl (aq)...

Now, I just need to understand this..
For the primary I said it does go under halogenation because it produces 1-chlorobutane + water

For the secondary I said it also goes under halogenation because it produces 2-chlorobutane + water

For the tertiary I said it doesn't go under halogenation because there is no Hydrogen available unless you break the carbon-carbon binding.

Am I right? Any explanations/suggestions? Are the products correct? Chemistry experts help please =)

Also, when those alcohols were mixed with the HCl (aq), what did it mean when cloudiness appeared...did it mean that if cloudiness appeared it went under halogenation or that if cloudiness appeared it didn't go under halogenation?

Answer 1

Your explanation about tertiary alcohols not being able to react is about oxidation, not halogenation. For halogenation, we are talking about a nucleophilic substitution reaction, and all three types can do this, although the mechanism changes from SN2 to SN1. The cloudiness is due to the fact that the haloalkane products are less soluble in water than the corresponding alcohols, because they can't hydrogen bond. What you saw was an emulsion forming.