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UPSC Combined Geo-Scientist

Chemist

  • 3 descriptive papers
  • 200 marks each
  • 3 h per paper

Mains Paper III covers analytical and organic chemistry.

UPSC Combined Geo-Scientist, Mains · 2017 · Mains Paper III

Q10(c). Hydroxyketone structure

Question

C₆H₁₂O₂: UV 283 nm (ε=27); IR 3450, 2900, 1705 cm⁻¹; ¹H 1.3(s,6H), 2.2(s,3H), 3.8(s,1H, D₂O-exchangeable), 2.5(s,2H). Off-resonance ¹³C is reported as two singlets, one triplet and one quartet, including 210 and 70 ppm. MS 116,58,43. Deduce structure.

Answer in brief

4-Hydroxy-4-methylpentan-2-one (diacetone alcohol), CH₃COCH₂C(OH)(CH₃)₂. The carbon multiplicity list omits a second quartet.

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CoversHydroxyketone structureCombined spectroscopy

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