I can second this book: written in 1939, but it hasn't dated at all.
Apart from being hilarious and great fun, it's also a suprisingly serious study of just how much technology, and I'm not talking about the modern stuff, is based on a huge pyramid of other skills and technologies which you simply can't leapfrog.
Mild spoilers follow:
Our hero, after being flung back in time to Rome in the year 535, is trying to prevent the fall of the late Roman Empire when it gets conquered by the Byzantines (actually the story's a lot more complex than that, so that's simplified). He tries to reinvent all sort of different pieces of military technology, and fails utterly --- turns out reliable gunpowder is really hard to make. His clocks won't keep time, his lenses aren't round, and he doesn't even both with electricity.
The innovations he eventually ends up successfully introducing? Distilled spirits (a great money-maker!), Arabic notation, double-entry notekeeping, and semaphores.