Question

The sulfuric acid–catalyzed reaction of isopentyl alcohol with acetic acid to form isopentyl acetate is performed. This reaction does not proceed to completion. After the reaction is heated under reflux for an hour, the product mixture is washed with aqueous sodium bicarbonate solution, and the organic layer is thoroughly dried. A distillation of the organic layer is then performed. Given the boiling points listed below, select the compound that will distill first.

Compound Boiling point, ℃
acetic acid 118
isopentyl acetate 142
isopentyl alcohol 130
sulfuric acid water 290

Answer 1

The correct option is acetic acid

Step-by-step explanation:

Distillation is the process of separating a mixture of substances based on differences in boiling points. During distillation, the compound with the lowest/least boiling point is distilled and collected first and then the one with the next least boiling point and it goes on like that.

From the explanation above, acetic acid has the least boiling point (in the organic layer) with 118°C and thus will distill first. This is then followed by isopentyl alcohol (130°C) and then isopentyl acetate (142°C) and finally sulfuric acid water (290°C).