How to Make Tert-Butyl Chloride

In this video, I show you how to make tert-butyl chloride from tert-butyl alcohol and hydrochloric acid. Tert-butyl alcohol is a type of molecule known as an alkyl halide. The term "alkyl" means that each carbon atom is bonded to 4 atoms (4 single bonds). The term "halide" means that there is a carbon-halogen bond, in this case a carbon-chlorine bond. Alkyl halides are pretty useful molecules because the halgoen atom can be exchanged for other atoms, molecules, or ions, producing a variety of different compounts.
*The IUPAC name for tert-butyl chloride is 2-chloro-2-methylpropane
This reaction is fairly straightforward: just mix hydrochloric acid with tert-butyl alcohol.
Despite the seemingly simple reaction, the mechanism is really interesting.
I explain the mechanism in the video (with diagrams!), but the fact that makes it interesting is that this mechanism only works for tertiary alcohols. It is possible to make primary and secondary alkyl chlorides, but the reaction doesn't happen at room temperature and is a lot more complex to carry out.

Huge thanks to James from masterorganicchemistry.com for letting me use his reaction mechanism diagrams! The link to that page is provided below:
masterorganicchemistry.com/2015/02/27/making-al…

Explanation of my issues with the graph: The graph's density values were way off from the density values I calculated, even after accounting for the uncertainty in my measuring equipment and calibrating my pipet and digital balance. I am currently using the analytical balances and pipets at my school to replicated the paper's procedure and see if the authors of the paper messed up (or if I just screwed something up without realizing it).
Learn more about Nucleophilic Substitution:

masterorganicchemistry.com/2015/02/27/making-al…

Learn more about SN1 reactions:

organic-chemistry.org/namedreactions/nucleophil…

Original procedure: orgsyn.org/Content/pdfs/procedures/CV1P0144.pdf

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