Suppose $J$ is an $n \times n$ Jordan block with eigenvalue $0$, what is the Jordan form of $J^2$?
My solution:
I squared the matrix, it follows that the eigenvalues are $0$ again, and $\dim(N(J^2)) = 2$, with eigenvectors $e_{n-1}$, $e_{n}$.
Therefore, the Jordan form of $J^2$ is an $(n-2) \times (n-2)$ block and two $1\times1$ blocks all with eigenvalue zero.
However, there is a hint with the question which says to treat odd and even values of $n$ separately but I fail to see why.
You're wrong. For example, $$ \pmatrix{0 & 1 & 0 \cr 0 & 0 & 1\cr 0 & 0 & 0\cr}^2 = \pmatrix{0 & 0 & 1\cr 0 & 0 & 0\cr 0 & 0 & 0\cr} \ \text{has Jordan form}\ \pmatrix{0 & 1 & 0\cr 0 & 0 & 0\cr 0 & 0 & 0\cr}$$ (a block of size $2$ and a block of size $1$) but $$ \pmatrix{0 & 1 & 0 & 0\cr 0 & 0 & 1 & 0\cr 0 & 0 & 0 & 1\cr 0 & 0 & 0 & 0\cr}^2 = \pmatrix{0 & 0 & 1 & 0\cr 0 & 0 & 0 & 1\cr 0 & 0 & 0 & 0\cr 0 & 0 & 0 & 0\cr}\ \text{has Jordan form}\ \pmatrix{0 & 1 & 0 & 0\cr 0 & 0 & 0 & 0\cr 0 & 0 & 0 & 1\cr 0 & 0 & 0 & 0\cr}$$ (two blocks of size $2$).