If I get my chocolate fix in the morning, will the caffeine still keep me awake at night?

Caffeine in chocolat. There really isn't that my much caffeine in chocolate, but there is some. There is also a related substance, theobromine. The half life of caffeine can range from 3-12 hours, meaning that with a single dose of chocolate in the morning at 7am, if you are on the 12-hour side, you will still have 1/2 of the caffeine around. Given the small amounts, it is not likely that it would keep you awake.
Highly unlikely. There is really just a tiny amount of caffeine in most chocolate. Unless you are unusually sensitive, it is unlikely to keep you awake no matter when you eat it. Certainly the effect could not last the many hours between the morning and bedtime.