Sentence 1: Watch him, so he won't go into shock when he wakes up.

Sentence 2: He is already awake
Is this second sentence entailed by the first?

Answer: no

Sentence 1: I seemed to see her for a moment as she was, a proud wild creature, as untamed by civilization as some shy bird of the hills.

Sentence 2: I was referring to a young woman.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: It's barbed tip pierced through.

Sentence 2: It's blunt tip failed to penetrate.
Is this second sentence entailed by the first?

Answer:
no