I know that we can find the first weak derivative for $f(x) = \lvert x \rvert$, which is $$w(x) = \begin{cases}-1 &x<0\\0&x=0\\1&x>0\end{cases}.$$But why is there no second weak derivative? If I try to find the first weak derivative of $w(x)$, I get that $$\int_{\mathbb{R}}v(x)\psi(x)\;dx = -\int_{\mathbb{R}}w(x)\psi'(x)\;dx = 2\psi(0).$$What does this mean? Why is there no $v$ such that $Dw = v$? I feel like I'm missing something and I'm not sure how to interpret this result.
Any help is appreciated!
The notion of weak derivative is a subset of the notion of distribution derivative. There is indeed a distribution second derivative to this function and congratulations, you found it! It is $2\delta_0$ where $\delta_0$ is the Dirac mass which verifies $$\left<\delta_0,\psi\right>=\psi(0).$$ You should have a look on some reference on distribution theory, which contains your weak derivative theory.