Show that the hare runs the sleepy tortoise is not a valid sentence. The grammar with start

Question:

Show that the hare runs the sleepy tortoise is not a valid sentence.
The grammar with start symbol sentence, set of terminals T = {the, sleepy, happy, tortoise, hare, passes, runs, quickly, slowly}, set of nonterminals N = {noun phrase, transitive verb phrase, intransitive verb phrase, article, adjective, noun, verb, adverb}, and productions:

Adjective †’ sleepy
Adjective †’ happy
Noun †’ tortoise
Noun †’ hare
Transitive verb †’ passes
Intransitive verb †’ runs
Adverb †’ quickly
Adverb †’ slowly