🇺🇸 AMC 8 ⇄ switch contest
1996 AMC 8 Stretch

Problem 10

Problem 10 · AMC 8 Stretch Core
Logic & Word Problems Geometry & Measurement proof-by-contradictionparity
Is it possible to draw a single straight line that crosses every one of the \(999\) sides of a \(999\)-sided polygon? Explain why or why not.
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Answer: No — it is impossible (a parity argument, since 999 is odd)
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Hint 1 of 4
Suppose it IS possible, and look for something that goes wrong (this is proof by contradiction). A straight line splits the plane into two sides — call them 'left' and 'right'.
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Hint 2 of 4
Walk around the polygon vertex by vertex. Every time you cross the line, you switch from one side to the other. So crossing a side means the two endpoints of that side are on opposite sides of the line.
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Hint 3 of 4
If the line crosses ALL 999 sides, then every pair of neighboring vertices is on opposite sides — the vertices must perfectly alternate left, right, left, right... all the way around.
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Approach: Proof by contradiction using parity
  1. Suppose, for contradiction, that one straight line crosses all 999 sides. The line cuts the plane into two halves.
  2. Walk around the polygon from vertex to vertex. Crossing a side means stepping over the line, switching half-planes, so a crossed side has its two endpoints on opposite sides.
  3. If every one of the 999 sides is crossed, the vertices must alternate left, right, left, right around the whole loop and return to the start.
  4. Returning to the start after alternating only works with an even number of vertices. Since \(999\) is odd, perfect alternation around the loop is impossible — a contradiction. So no such line exists.
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