Q:

Which preposition should I use ahead of "awake"?

In the following sentence, which preposition should I use before "awake"?

I spent all last night by (???) awake.

In order to mean: I was awake all the last night.

A:

Awake is not a noun, so you wouldn't usually have a preposition there. Instead, you'd simply say:

I was awake all last night. 

If you wanted to end with a prepositional phrase, you'd need to find one that ends with a suitable noun. The preposition you would choose would likely depend on the verb choice. Here are some examples:

Last night, I wrestled with sleeplessness.  
Last night, I had a bout of insomnia. 
Last night, I was kept awake by worry. 

In my mind, though, those are rather specialized sentences, and would only be used if you wanted to supply additional information about why you were awake all night. If you just want to tell folks that you didn't sleep, just tell them; for example:

I didn't sleep a wink last night. 

