UPSC Combined Geo-Scientist, Mains · 2018 · Mains Paper III

Q10(d). Phenethyl alcohol spectra

10 marks
Topic: Spectroscopic methods of analysis
Answered

Question

Identify: UV 262 nm; IR 3340, 3000, 1040 cm⁻¹; ¹H 1.9(s,1H, exchangeable), 2.9(t,2H), 3.8(t,2H), 7.2–7.4(m,4H); ¹³C 39,62,126,128,129,139; MS 122,92,91.

Answer in brief

2-Phenylethanol, PhCH₂CH₂OH; the aromatic integration should be 5H, not the printed 4H.

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CoversPhenethyl alcohol spectraStructure elucidation

All parts of Question 10

10(a) Phenolic OH band shapes5 marks
10(b) Cyclic ether identification5 marks
10(c)(i) Most downfield proton2 marks
10(c)(ii) Highest carbonyl frequency2 marks
10(c)(iii) Odd nominal molecular mass2 marks
10(c)(iv) Most upfield carbon2 marks
10(c)(v) Longest-wavelength diene band2 marks
10(d) Phenethyl alcohol spectra10 marks