Question

Problem 7: UV: no absorption peaks > 220 nm 13C NMR(in ppm): 22.9, 28.9, 29.3, 34.6, 69.3, 176.2 MS: % abundance m/z 76 55 114(M) 100 13 -1.6-1.9 (6H) 82.65 (2H) 84.25 (2H) 'H NMR spectrum (CDCI) SOURCE: Reprinted with permission of Aldrich Chemical. IR spectrum SOURCE: OBIO-RAD Laboratories, Sadtler Division % Transmittance 3500 3000 1000 500 2500 2000 1500 Wavenumber (cm')

WHAT IS THE COMPOUND??

Answer 1

The unknown is 6-hexanolide (also called as Epsilon-caprolactone) (IUPAC: oxepan-2-one)

IR:

2850-3000 cm-1, strong, sp3 C-H stretch

1350-1480 cm-1, medium, multiple bands, sp3 C-H bending

1735-1750 cm-1, strong, ester C=O stretch

1000 - 1300 cm-1, two bands or more , strong, ester C-O stretch

CNMR:

Assign. ppm osum WNP 176.22 69.30 34.57 29.34 28.93 22.99

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