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The cyclic ether tetrahydrofuran (THF) can be synthesized by treating 4-chloro-1-butanol with aqueous sodium hydroxide (see below). Propose a mechanism for this reaction. |
Answer» Solution :Removal of a proton from the HYDROXYL group of 4-chloro 1-butanol gives an alkoxide ion that can then REACT with itself in an intramolecular `S_(N)2` reaction to form a ring.  EVEN though treatment of the alcohol with hydrox ide does not favor a large equilibrium concentration of the alkoxide, the alkoxide anions that are present react rapidly by the intramolecular `S_(N)2`reaction. As alkoxide anions are consumed by the substitution reaction, their equilibrium concentration is REPLENISHED by deprotonation of additional alcohol molecules, and the reaction is drawn to completion. |
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