My brother asked me this problem, and he is studying ninth-grade. I can't solve it using primitive tools of pure geometry. Hope someone can give me a hint to solve it. Thanks.
Given a circle $(O, R)$ and $A$ is outside $(O)$ such that $OA > 2R$. Draw two tangents AB, AC of $(O)$. Let $I$ is midpoint of AB. Segment OI intersects with (O) at M. AM intersects with (O) at N, $N \neq M$. NI intersects with BC at Q. Prove that MQ perpendicular with OB
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I'm lucky to find this beautiful solution, and it only uses 9th-grade level knowledge to solve. Here is the solution
Let P and R are intersections of BC with OI and AM, correspondingly. Let S is the reflection of M through I.
Firstly, even using 9th-grade level, we can easily prove that ${RM \over RN} = {AM \over AN}$, therefore ${RM \over MA} = {RN \over AN}$. I is the same midpoint of both BA and MS, hence BSAM is a parallelogram, therefore BS is parallel to MR.
We have this equation chain:
Therefore, we must have that PN is parallel to BA. Therefore, we have this equation chain:
Therefore, QM is parallel to BA. The problem is solved.