Q10(d)(ii). Structure from IR, ¹H and ¹³C NMR: C₁₀H₉NO₂
An unknown organic compound with molecular formula C₁₀H₉NO₂ gives the following spectral data: IR: 2210, 1724 cm⁻¹; ¹H NMR: δ 1.4 (t, J = 7.1 Hz, 3H), 4.4 (q, J = 7.1 Hz, 2H), 7.7 (d, J = 7.0 Hz, 2H), 8.2 (d, J = 7.0 Hz, 2H); ¹³C NMR: δ 16, 62, 118, 119, 125, 126, 127, 168. Identify the structure and justify your answer.
Model answer
The free solution for 2024 answers questions 1, 4, 5, 6, 7 and 9, the ones picked in its time plan. Question 10 is answered in full in the Geo-Scientist Chemistry Paper III, 2021 to 2025 book, with every part of every paper.
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UPSC Combined Geo-Scientist (Main) Chemistry Paper III: Model Answers 2021 to 2025
- All ten questions of each paper, with the question printed above its answer
- Instruments drawn as labelled diagrams, numericals worked with units
- Topic-wise weightage and a topic-wise index
Coversstructure elucidationnitrile IRester carbonylpara-disubstituted benzeneethyl ester
All parts of Question 10
- 10(a)(i) Anisole with dibromocarbene: ring expansion to a tropone5 marks
- 10(a)(ii) Benzophenone with aluminium isopropoxide at 250 °C5 marks
- 10(b) Structure from ¹H and ¹³C NMR: C₁₅H₁₄O5 marks
- 10(c) Band width and colour; ν(C=O) of acids and ketones5 marks
- 10(d)(i) Mass spectral fragmentation of an ester and a cyclohexene5 marks
- 10(d)(ii) Structure from IR, ¹H and ¹³C NMR: C₁₀H₉NO₂5 marks