Does Tom catch Jerry?
Let $x=1$ be the wall, let Tom start at $(0,0)$, Jerry at $(1,0)$ upwards, and assume that both have the same speed $1$. Tom's orbit is then a graph curve $$\gamma: \quad x\mapsto \bigl(x,y(x)\bigr)\qquad(0\leq x<1)\ ,$$ whereby $y(0)=y'(0)=0$. At any point $(x,y)\in\gamma$ we have $$y'={\int_0^x\sqrt{1+y'^2}\>dx -y\over 1-x}\ .\tag{1}$$ One arrives at this equation by the following argument: When Tom is at $(x,y)$ he has run the length $s:=\int_0^x\sqrt{1+y'^2}\>dx$ so far. Therefore Jerry is at $(1,s)$ now, and this enforces $(1)$.
From $(1)$ we get $$(1-x)y'+y=\int_0^x\sqrt{1+y'^2}\>dx\qquad(0\leq x<1)\ .$$ In order to get rid of the integral we take the derivative with respect to $x$ and separate variables: $${y''\over\sqrt{1+y'^2}}={1\over 1-x}\ .$$ This leads to $$\log\bigl(y'+\sqrt{1+y'^2}\bigr)=\log{1\over1-x}+C\ ,$$ and the initial condition $y'(0)=0$ immediately gives $C=0$. We solve for $y'$ and obtain $$y'={1\over2}\left({1\over 1-x}-(1-x)\right)\ .$$ One more integration then gives $$y(x)={x^2\over4}-{x\over2}+{1\over2}\log{1\over 1-x}\qquad(0\leq x<1)\ .$$ This is the explicit shape of $\gamma$. In order to compute how far Tom is staying behind in the limit we have to compute the limit for $x\to 1-$ of $$\int_0^x\left(\sqrt{1+y'^2(x)}-y'(x)\right)\>dx=\int_0^x(1-x)\>dx=x-{x^2\over2}\ .$$ It follows that Tom stays ${1\over2}$ behind in the limit.
See to the essence of the problem so you can avoid calculations:
No. Of course Tom will never catch Jerry.
- Jerry's horizontal speed is always $v_x=1$.
- Tom's horizonal speed begins $v_x<1$ and is always $v_x \le 1$.
QED.
The problem is simplified considerably if we consider the vector from Tom to Jerry.
So let $\vec r=\pmatrix{x\\y}$ be the vector from Tom to Jerry, with $r=|\vec r|=\sqrt{x^2+y^2}$. Then
\begin{eqnarray*} \dot x&=&-\frac xr+1\;,\\ \dot y&=&-\frac yr\;, \end{eqnarray*}
and
\begin{eqnarray*} \dot r&=&\frac{x\dot x+y\dot y}r\\ &=&\frac xr-1\\ &=&-\dot x\;. \end{eqnarray*}
Thus $r+x$ is constant. Initially $x=0$ and $r=1$, so the sum is $1$. In the limit, $x=r$, so both are $\frac12$.
This answers questions $1$ and $2$. To answer question $3$, you can introduce $\phi$ with $x=r\cos\phi$ and $y=r\sin\phi$ and calculate $\frac{\mathrm dr}{\mathrm d\phi}=\frac{\dot r}{\dot \phi}$ from $\dot x$ and $\dot y$. The result is
$$ \frac1r\frac{\mathrm dr}{\mathrm d\phi}=\tan\frac\phi2\;, $$
and integrating yields $r=\lambda\cos^{-2}\frac\phi2$. The initial condition $r=1$, $\phi=\frac\pi2$ yields $\lambda=\frac12$, so the trajectory is
$$ r=\frac1{2\cos^2\frac\phi2}\;. $$
Substituting $\phi=0$ again yields $r=\frac12$ in the limit.