Jeopardy Isomerism

Last night on Jeopardy! there was some organic chemistry sloppiness that I, a former organic chemistry instructor, feel a desperate compulsion to sort out.

The sloppiness occurred in the Final Jeopardy segment. The Final Jeopardy category was "In the Dictionary" and the Final Jeopardy clue was:

This adjective can mean "delicate", "heavenly", or, in chemistry, "related to C₄H₁₀O".

The correct question is "What is ethereal?" "Ethereal" and the "related to C₄H₁₀O" part of the clue point to ether - more specifically diethyl ether (ethoxyethane), CH₃CH₂OCH₂CH₃ - whose molecular formula is indeed C₄H₁₀O. However, there are actually six other compounds that C₄H₁₀O could refer to:

Alcohols
(1) butanol (1-butanol): CH₃CH₂CH₂CH₂OH
(2) isobutanol (2-methyl-1-propanol): (CH₃)₂CHCH₂OH
(3) sec-butanol (2-butanol)*: CH₃CH₂CH(OH)CH₃
(4) tert-butanol (2-methyl-2-propanol): (CH₃)₃COH
(*I am ignoring R/S stereoisomerism here.)
Ethers
(5) methyl propyl ether (1-methoxypropane): CH₃OCH₂CH₂CH₃
(6) isopropyl methyl ether (2-methoxypropane): CH₃OCH(CH₃)₂

(Hmmm, maybe we could make an exam question out of this...)

In sum, the Final Jeopardy clue should have been disambiguated by specifying ether's condensed structure vis-à-vis its molecular formula:

This adjective can mean "delicate", "heavenly", or, in chemistry, "related to CH₃CH₂OCH₂CH₃".

Clearly, it's time to send Alex and the Clue Crew back to school for an organic chemistry refresher. ;-)

There. I feel better now.