Tetrahydrofuran or Diethyl Ether – Which to Use?

Tetrahydrofuran (C4H8O) is a heterocyclic hydrocarbon. One of the carbon atoms of a cyclopentane ring (along with its two hydrogen atoms) is replaced by an atom of oxygen. THF is an ether. It's frequently used for its solvent properties. In certain organometallic reactions, tetrahydrofuran replaces all or part of the standard solvent diethyl ether, (C2H5-O-C2H5), written in chemists' shorthand Et-O-Et. Tetrahydrofuran Vs. Diethyl Ether Although THF is essentially diethyl ether gone cyclic, its physical properties differ somewhat. A prime example of that relates to hydrogen bonding. Although both molecules possess an electron-rich oxygen atom, in THF, the oxygen is openly exposed. The ring can twist, but that's about it. The hydrocarbon portions of ethyl ether¹ have much greater freedom of motion. They can sweep around, making hydrogen bonding easier to…
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