So we did a preparation of t-pentyl Chloride experiment in class the other day u

Question

So we did a preparation of t-pentyl Chloride experiment in class the other day using t-pentyl alcohol, HCL, Aqueous sodium Bicarbonate, and calcium chloride as the drying agent.

Little confused on a few of these questions

Aqueous sodium bicarbonate was used to wash the crude t-pentyl chloride, what was the purpose of this wash (show reactions) and why would it be undesirable to wash with aqueous sodium hydroxide instead?

Why is calcium chloride used as the drying agent instead of sodium or magnesium sulfate?

The drying agent is an anhydrous ionic solid, why do we need to remove it before distillation? (hint- what happens to a hydrate when heated)

Explanation / Answer

Aqueous sodium carbonate is used as a wash to eliminate polar impurities (they are washed off with the polar solution). If you were to use sodium hydroxide, it would be too polar and act as a base (giving an elimination product) or a nucleophile (giving a substitution reaction).

By using CaCl2...you insure that you will not obtain another product if the sulfate were to act as a nucleophile or base. In other words, If chlorine replaces chlorine you still have the same product...but if the sulfate replaces the chlorine, your left with a by product.

The anhydrous ionic solid is used to soak water up...if you heat it you will just release water and you may obtain the alcohol again.

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