Let's analyze the NMR data and the structures: ## NMR Data for Compound 9: ``` δ 7.31–7.24 (m, 1H), 7.20–7.15 (m, 1H), 7.09 (m, 1H), 7.00 (m, 1H), 3.84 (s, 3H), 3.80 (s, 3H) ``` - **Aromatic protons:** Four multiplets in the range of 7.00–7.31 ppm (4H total). - **Methoxy groups:** Two singlets around 3.8 ppm, each integrating to 3H. ## Structures to Match We have four structures, but let's match the pattern: ### Key Observations: - The compound has **two methoxy groups** (indicated by the two singlets). - The aromatic region integrates to 4 protons, suggesting a **disubstituted benzene ring**. ### Analyzing Each Structure: #### Structure 1: - Contains a fluorine substituent and two methoxy groups. - The pattern fits: 4 aromatic protons, two methoxy groups. #### Structure 2: - Contains a hydroxy group and two methoxy groups. - A hydroxy proton would show up as a singlet downfield (usually 9–12 ppm), which is **not present** in the NMR data. #### Structure 3: - Contains two methoxy groups and a thioether substituent. - The sulfur atom would shift the aromatic protons, but the NMR does not indicate a strong deshielding effect typical for S-substituted aromatics. #### Structure 4: - Contains an ester (COOCH₃) in addition to two methoxy groups. - The additional methyl ester group should show another singlet near 3.7–3.9 ppm for the COOCH₃, leading to three singlets in the 3.8 ppm range, but only two are observed. ## **Conclusion** **Structure 1** best matches the NMR data: - Two methoxy groups (two singlets). - Four aromatic hydrogens in the correct region (multiplets). - No extra exchangeable protons (like OH). - No extra methyl groups (as in methyl ester). --- ### Answer: **The NMR data in question 9 corresponds to structure 1 in the image.** --- ####  *Alt text: Structure 1 has a fluoro and two methoxy groups on a benzene ring with an ester group.* Let me know if you want the assignment for question 10 as well!