Conundrum
wiktionary
A word of unknown origin with several variants, gaining popularity for its burlesque imitation of scholastic Latin, as hocus-pocus or panjandrum. If there is more to its origin than a nonce coinage, Anatoly Liberman suggests the best theory is that connecting it with the Conimbricenses, 16th c. scholastic commentaries on Aristotle by the Jesuits of Coimbra which indulge heavily in arguments relying on multiple significations of words. [1]
etymonline
conundrum (n.)
1590s, an abusive term for a person, perhaps meaning "a pedant;" c. 1600, "a whim;" 1640s, "pun or word-play," a word of unknown origin, said in 17c. to be Oxford University slang. Perhaps the sort of ponderous mock-Latin word that was once the height of humor in learned circles; Skeat suggests Latin conandrum "a thing to be attempted" as the source. Also spelled quonundrum.
From 1745 as "a riddle in which some odd resemblance is proposed between things quite unlike, the answer often involving a pun." (An example from 1745: "Why is a Sash-Window like a Woman in Labour? because 'tis full of Panes").
