When we did a SN1 reaction forming t-amyl chloride from t-amyl alcohol and HCl (cleaning the crude sample with NaCl and NaHC03, using CaCL2 as a drying agent) we observed a low boiling fraction around 40 degrees Celsius during distillation.

Question: What might be present in this fraction and should it be included in the purified product. WHy or Why not?

3 answers

The alcohol boils at 102 C.
The chloride boils at 85-86 C.
So with that much difference in boiling with a fraction at about 40 C, I don't think it should be included with the product. That large a boiling point different must mean the 40 C fraction is something different. Could it be 2-methyl-2-butene or a similar product? That has a boiling point of 39 C. Check my data to make sure I didn't misread a table.
That makes sense because in this SN1 reaction a E1 reaction competes with the carbocation intermediate and forms a side product...which is 2-methyl-2-butene.
But I don't understand why or why not the fraction is included in the product. Is it just because their boiling points are so far apart? Hence, what criteria are used to determine if its included or not? When would something be included?
If you are distilling something to purify it, why would you want to add something different and deliberately contaminate a product?