Advanced Organic Chemistry Practice Problems |top| May 2026

Staring at a page of skeletal structures and curved arrows can feel a bit like trying to read a map of a city that hasn’t been built yet. If you’re diving into Advanced Organic Chemistry, you’ve moved past simple memorization and into the realm of "chemical intuition."

Spectroscopy

Art of Problem Solving (David Evans): Excellent for retrosynthetic challenges. advanced organic chemistry practice problems

Problem 7: NMR-Based Structural Elucidation

Question:
A compound C₁₀H₁₀O₂ has (^13\textC) NMR: δ 197, 165, 152, 139, 132, 128 (2C), 126 (2C), 122, 60. (^1\textH) NMR: δ 7.9 (d, J=16 Hz, 1H), 7.5–7.3 (m, 5H), 6.5 (d, J=16 Hz, 1H), 4.3 (q, J=7 Hz, 2H), 1.4 (t, J=7 Hz, 3H). IR: 1715, 1680 cm⁻¹. Identify and explain the unexpected coupling constant. Staring at a page of skeletal structures and