[proofplan]
For part (1), we show $U \subseteq U^{00}$ directly by checking that $\mathrm{ev}(u)$ annihilates every element of $U^0$, then conclude equality by the Dimension of Annihilator theorem applied twice.
For part (2), we verify $\alpha^{**} \circ \mathrm{ev}_V = \mathrm{ev}_W \circ \alpha$ by evaluating both sides at arbitrary vectors and functionals, using the definitions of the dual map and the evaluation map.
[/proofplan]
[step:Show $U \subseteq U^{00}$ under the canonical identification $V \cong V^{**}$]
For any $u \in U$ and $\theta \in U^0$:
\begin{align*}
\mathrm{ev}(u)(\theta) = \theta(u) = 0,
\end{align*}
since $\theta \in U^0$ means $\theta$ vanishes on $U$.
So $\mathrm{ev}(u) \in (U^0)^0 = U^{00}$.
Under the identification $V \cong V^{**}$ via $\mathrm{ev}$, this gives $U \subseteq U^{00}$.
[/step]
[step:Conclude $U^{00} = U$ by dimension counting]
By the [Dimension of Annihilator](/theorems/420) applied to $U \subseteq V$:
\begin{align*}
\dim U^0 = \dim V - \dim U.
\end{align*}
Applying the same theorem to $U^0 \subseteq V^*$:
\begin{align*}
\dim U^{00} = \dim V^* - \dim U^0 = \dim V - (\dim V - \dim U) = \dim U.
\end{align*}
Since $U \subseteq U^{00}$ and $\dim U = \dim U^{00}$, we have $U = U^{00}$.
[guided]
The containment $U \subseteq U^{00}$ was established in the previous step. To upgrade this to equality, we compare dimensions.
The [Dimension of Annihilator](/theorems/420) states that for a subspace $W$ of a finite-dimensional space $X$, $\dim W^0 = \dim X - \dim W$. Applying this to $U \subseteq V$:
\begin{align*}
\dim U^0 = \dim V - \dim U.
\end{align*}
Now $U^0$ is a subspace of $V^*$, and $U^{00} = (U^0)^0$ is taken inside $V^{**}$. Applying the dimension formula again to $U^0 \subseteq V^*$:
\begin{align*}
\dim U^{00} = \dim V^* - \dim U^0 = \dim V - (\dim V - \dim U) = \dim U.
\end{align*}
We used $\dim V^* = \dim V$ from the [Dimension of Dual Space](/theorems/415). Since $U \subseteq U^{00}$ and both have dimension $\dim U$, equality holds: $U = U^{00}$.
The double annihilator thus acts as an involution on the lattice of subspaces of $V$ (in finite dimensions). This is the algebraic counterpart of the fact that in a Hilbert space, $W^{\perp\perp} = \overline{W}$ (the double orthogonal complement recovers the closure, which for finite-dimensional subspaces is the subspace itself).
[/guided]
[/step]
[step:Verify $\alpha^{**} = \alpha$ under the canonical identifications]
Under the identifications $\mathrm{ev}_V: V \xrightarrow{\sim} V^{**}$ and $\mathrm{ev}_W: W \xrightarrow{\sim} W^{**}$, we must show $\alpha^{**} \circ \mathrm{ev}_V = \mathrm{ev}_W \circ \alpha$.
For any $v \in V$ and $\theta \in W^*$:
\begin{align*}
(\alpha^{**}(\mathrm{ev}_V(v)))(\theta) &= \mathrm{ev}_V(v)(\alpha^*(\theta)) = \alpha^*(\theta)(v) = \theta(\alpha(v)) = \mathrm{ev}_W(\alpha(v))(\theta).
\end{align*}
Since this holds for all $\theta \in W^*$, we have $\alpha^{**}(\mathrm{ev}_V(v)) = \mathrm{ev}_W(\alpha(v))$ for all $v \in V$.
That is, $\alpha^{**} \circ \mathrm{ev}_V = \mathrm{ev}_W \circ \alpha$.
Identifying $V$ with $V^{**}$ and $W$ with $W^{**}$ via these evaluation maps, $\alpha^{**} = \alpha$.
[guided]
The claim $\alpha^{**} = \alpha$ should be understood as a commutativity statement for the diagram
\begin{align*}
V \xrightarrow{\alpha} W \xrightarrow{\mathrm{ev}_W} W^{**}, \qquad V \xrightarrow{\mathrm{ev}_V} V^{**} \xrightarrow{\alpha^{**}} W^{**}.
\end{align*}
We verify the two paths agree. Take $v \in V$ and $\theta \in W^*$. Following the bottom path:
\begin{align*}
\alpha^{**}(\mathrm{ev}_V(v))(\theta) = \mathrm{ev}_V(v)(\alpha^*(\theta)),
\end{align*}
by definition of the dual map $\alpha^{**}$ (precompose with $\alpha^*$). Now $\mathrm{ev}_V(v)(\alpha^*(\theta)) = \alpha^*(\theta)(v)$ by definition of the evaluation map, and $\alpha^*(\theta)(v) = \theta(\alpha(v))$ by definition of $\alpha^*$. Following the top path: $\mathrm{ev}_W(\alpha(v))(\theta) = \theta(\alpha(v))$. The two expressions coincide, confirming the diagram commutes.
Since $\mathrm{ev}_V$ and $\mathrm{ev}_W$ are isomorphisms (by the [Canonical Isomorphism to Double Dual](/theorems/423)), this says $\alpha^{**} = \mathrm{ev}_W \circ \alpha \circ \mathrm{ev}_V^{-1}$, which under the identification is simply $\alpha^{**} = \alpha$.
[/guided]
[/step]