[psychoNOT]

A question asks why the synthesis of t-amyl chloride from t-amyl alcohol and HCl forms two layers as the reaction proceeds.  I said t-amyl chloride is insoluble in water, because the electron-withdrawal normally caused by the Cl of the C-Cl bond is counteracted by the three alkyl groups which donate electrons to make the C of the C-Cl bond less electron deficient.  This makes it much less polar, and therefore very insoluble in water.  The alcohol is soluble in water because of its ability to hydrogen bond, so the t-amyl chloride forms an organic layer which separates from the aqueous layer which contains the alcohol.  This was observed, and I think my logic makes sense but I would appreciate a confirmation.
Thanks!

[Smrt guy]

It's not about the polarity of the C-Cl bond so much as the hydrogen bonding.