For all , find the largest positive integer such that we can select diagonals from the diagonals of a regular -gon so that any two of the selected diagonals, if they intersect inside the regular -gon, must be perpendicular to each other.
Solution
Solution: If is odd, then ; if is even, then .
1. First we prove the case where is odd.
a. Claim. No two diagonals within a regular -gon are perpendicular.
Suppose diagonals and are perpendicular. Draw the perpendicular bisector of , which meets the regular -gon at vertex (note that since is odd, exists). Let be the point symmetric to on the regular -gon:
- Note that since is odd, cannot be a vertex of the regular -gon.
- However, by symmetry, it is easy to see that . This means must be a vertex of the regular -gon.
Contradiction!
b. By the above Claim and the problem's assumption, these diagonals must not intersect inside the polygon; in other words, they must all emanate from the same endpoint, and there are diagonals emanating from the same endpoint, which proves the claim.
(a) We first prove a stronger result by induction: for all , if we can select diagonals satisfying the problem's condition from a cyclic -gon, then . This is obvious when . Now, suppose holds for ; then when , we discuss two cases:
Case 1. Among these diagonals, there is one that does not intersect any other diagonal inside the polygon. This diagonal divides the regular -gon into an -gon and an -gon (). Without loss of generality, suppose the -gon lies entirely on one side of some diameter of the circumscribed circle of the regular -gon; then it is easy to see that no two diagonals within this -gon can be perpendicular, so within the -gon we can only choose non-intersecting diagonals. As in the discussion of 1.(a) above, the maximum possible number of these is .
On the other hand, by the induction hypothesis, at most diagonals can be chosen within the -gon, so in total at most diagonals can be chosen.
Case 2. Every one of these diagonals is perpendicular to at least one other. Let and be a pair of perpendicular diagonals; then they divide the circle into four regions:

- If there is another diagonal that is not perpendicular to either or , then its two endpoints must both belong to the same region (otherwise it would intersect or ).
- If we take two other intersecting diagonals and , neither of which is perpendicular to or , then their endpoints must both lie in the same region. However, it is easy to see that if the endpoints of two diagonals both lie in the same region, they cannot be perpendicular (as shown in the figure), a contradiction.
- Moreover, based on our assumption that every one of these diagonals is perpendicular to at least one other, these diagonals can only be parallel to or .
Now, let be the longest diagonal among these diagonals that is parallel to ; it is easy to see that none of the other diagonals can share an endpoint with . Similarly, let be the longest diagonal among these diagonals that is parallel to ; it is easy to see that none of the other diagonals can share an endpoint with . Excluding the four endpoints of and , each of the remaining vertices can be the endpoint of at most two diagonals (since these diagonals must all be parallel to or ), so at most
diagonals can be chosen. This proves the claim.
(b) Finally, we construct a selection achieving : select two points and of the regular -gon. Choose:
- ;
- Let and be the two vertices to the left and right of . Choose , and , where is perpendicular to .
- Let and be the two vertices to the left and right of . For all remaining vertices
choose .
In total there are diagonals.