Which reactant, on treatment with aqueous sodium hydroxide, gives the cyclic ether shown by an intramolecular Williamson reaction?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The ether is tetrahydrofuran. Hydroxide forms the alkoxide, which displaces chloride in the same molecule. Ring closure to a five-membered ring needs four carbons between the oxygen and the halogen-bearing carbon, i.e. 4-chlorobutan-1-ol. 3-Chloropropan-1-ol would give oxetane, 5-chloropentan-1-ol would give a six-membered ring, and 2-chlorobutan-1-ol would give an epoxide.

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