ANSWER

Step-by-step explanation
First, let us make a sketch of the problem:
The envelope is shaped like a rectangle.
The maximum possible length of the pencil is the length of the diagonal of the envelope.
To find the length of the diagonal, apply the Pythagoras theorem:

where hyp = hypotenuse
a, b = legs of the triangle formed by the diagonals and the sides of the envelope.
Therefore, for the question, we have that:
![\begin{gathered} p^2=5^2+8^2 \\ p^2=25+64 \\ p^2=89 \\ p=\sqrt[]{89} \\ p\approx9.4in \end{gathered}](https://img.qammunity.org/2023/formulas/mathematics/college/29upx8tzv7gi7p9il53ih6h0exudddbydj.png)
The maximum possible length of the pencil is 9.4 inches.