Alcohol 6:

Problem

Solution

Thionyl chloride (SOCl₂; bp 76°) reacts with 3-methyl-1-butanol 1 to give 1-chloro-3-methylbutane 2. Pyridine is used as a catalyst to generate free chloride ion. The other products of the reaction are SO₂ and HCl, which are both gases at ambient temperature. Write a mechanism, then click here.