Oh oh oh, this is so much fun: I like the idea of having a dissertation for dessert nom nom nom, ha ha.
In terms of the Latin, a common meaning of the uncompounded noun sertum, the participle of sero (meaning “to arrange, interweave” esp. to arrange in an elegant way) is a FLOWER ARRANGEMENT, a garland of flowers! Latin serta means “(flower) arrangement, a garland, a crown of flowers,” etc.
So if you are riffing on dissertation, you can have dessert AND flowers.
And with assert you are tapping into an INCREDIBLY weird and powerful aspect of Roman society because it was absolutely a slave society. To be “asserted” meant to be asserted, inserted, arranged in a social sense, i.e. to be a slave in someone’s household or, if you were lucky, to be declared to be free. And the “assertor” was the legal official who could pronounce someone’s assertion, whether they were slave or free! Check out the fascinating dictionary entry here:
ASSERTOR: one who formally asserts that another is free or a slave.
I. A restorer of liberty. Figuratively, a defender, protector, deliverer, advocate
II. He who claims or declares one to be a slave
The original meaning of Latin assertio (our “assertion”) was “a formal declaration that one is a freeman or a slave”
If you poke hard enough at pretty much any Latin word, you will find either money or slaves or both.