4-Bromobutan-1-ol is treated with one equivalent of $NaH$ in dry THF. The major product, formed by an intramolecular SN2 reaction, is

Aoxetane
Bbut-3-en-1-ol
Cbutane-1,4-diol
Doxolane (tetrahydrofuran)

Answer: D

NaH

converts the

OH

group into the alkoxide

- O - CH X_{2} CH X_{2} CH X_{2} CH X_{2} Br

. The alkoxide oxygen then attacks the

C - Br

carbon from the back in an internal Williamson reaction. Ring closure involves the oxygen and four carbons, giving the five-membered cyclic ether oxolane; oxetane would need 3-bromopropan-1-ol.

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4-Bromobutan-1-ol is treated with one equivalent of NaH in dry THF. The major product, formed by an intramolecular SN2 reaction, is

Answer: D

More questions on Reactions of alkyl halides with nucleophiles

4-Bromobutan-1-ol is treated with one equivalent of $NaH$ in dry THF. The major product, formed by an intramolecular SN2 reaction, is