In this chapter, Moses lists the blessings of obedience and the curses of disobedience.
As I mentioned in my commentary on the prior chapter, this is another part of the Hittite suzerainty treaty, so its presence here is part of the ritualistic and legal structure of Deuteronomy.
A few things to note. First, the blessings and curses in this chapter are directed at the nation as a whole, not to specific individuals. Although the blessings largely "trickle down" to the people in the nation, we can easily see that many of them are corporate blessings, such as the promise of military victory over other nations (v. 7), that do not have a straightforward application as a blessing upon specific individuals. From this and from other language in the covenant (Ex 19:8 is one of many examples), we can see that the promise is for the nation as a collective entity. This also explains the common refrain of "purging the evil from your midst" (Deut 13:5, 17:7, 17:12, 19:19, etc). The idea is that the nation as a whole must remain pure in order for the nation as a whole to maintain the covenant. If there is any man in Israel who is not following the LORD, to some extent his sin is imputed over the whole nation. Anyone who sins must be purged so that the nation as a whole may avoid wrath. We see this very clearly in the book of Joshua with the sin of Achan, and I will discuss that in more depth when we get there.
I'm emphasizing this point because in American culture at least, people can be very individualistic in how they view the world and think of their own covenant, their own sin, their own blessings and curses. The bible does have some parts where it speaks in very individualistic terms (e.g. Deut 24:16), but the covenant with Israel is not one of those places. Here it is being very explicitly corporate, and that's probably something my readers may not have frequently internalized.
The second point I'd like to address is that the section with curses is significantly longer than the section with blessings. I found this asymmetry very peculiar the first time I read this chapter. It violates my sense of aesthetics. Generally, the way that I've understood this chapter is that Moses is anticipating rebellion on their part and is elaborating because he thinks it's the more likely outcome. Also, the curses are also likely meant to foreshadow Israel's future because of the anticipated rebellion. In particular, Israel is later going to be conquered and exiled from the promised land as a result of their breaking the covenant with the LORD, and Moses is predicting this exile.
At this point, having read through Numbers, we have already seen Israel rebel on many occasions and drifted perilously close to judgment and disaster. That Israel would continue sinning and rebelling against God is hardly a daring prediction, and in this case it is quite correct.
The other thing I remember when I first read this passage is that I really wanted Israel to obey God and attain the covenantal blessing. It's like when you're watching a movie and you always want the characters to get happy endings. I wanted Israel to have a happy ending, to skip past the numerous disasters and misfortunes of the covenantal curse, and I regret to say that this is not what happens. It's a pretty sad story, to be honest. Fortunately, everything will change when we get to the New Testament.
As an additional minor note, Moses also refers to the future king again, which is why many scholars (who reject prophecy a priori) use this passage to give a late date to Deuteronomy, because later there will be a king in Israel, and these scholars assume that this passage could only have been written after the events it portends.
Anyway, I don't feel any particular desire to comment on the details of the curses or blessings. It's a fairly comprehensive list of plague, pestilence, famine, warfare, slavery, exile and so on, ending with despair, humiliation and a return to Egypt, the full and final reversal of the covenantal blessing and the Exodus from slavery. Everything that the LORD has done to this point is part of the covenant, so if the covenant is rejected then the people will be sent back to Egypt.