B.
4-Penten-1-ol. A 2-l. three-necked flask containing
112 g. (4.87 moles) of powdered sodium (Note
4) under
700 ml. of anhydrous ether is fitted with a mechanical stirrer, a separatory funnel, and a
reflux condenser with a drying tube. A few milliliters (2–3) of a mixture of
300 g. (2.5 moles) of tetrahydrofurfuryl chloride and 300 ml. of anhydrous ether is added to the rapidly stirred suspension. A vigorous reaction occurs, and the solution turns blue. The remainder of the solution of the chloride is then added dropwise over a period of 5 hours, during which time the flask is cooled in an ice bath (Note
5). When the addition is complete, stirring is continued for 2 hours. The suspension is decanted from any
sodium that remains (Note
6) into a dry beaker and decomposed with sufficient ice water to give two liquid layers. The
ether layer is separated and dried over
magnesium sulfate. After the removal of the ether by distillation on a
steam cone, the residue is distilled. The yield of
4-penten-1-ol boiling at
134–137° is
161–178 g. (
76–83%).