(i) Calculate the double bond equivalents (DBE) for each molecule. 

(ii) Assign the 1H NMR spectra completely, rationalise the number of peaks, relative integral, their multiplicity or splitting pattern where appropriate. 

(iii) Rationalise the 13C NMR spectra. 

(iv) Rationalise all numbered peaks in the mass spectra and IR spectra. 

(v) Provide a brief logical explanation for how you arrived at unambiguous structures.

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Problem 14 IR Spectrum (iquid fim) 3354 4000 3000 2000 1600 1200 800 V (cm") 100 Mass Spectrum 45 80 No significant UV absorption above 220 nm M*- 60 (< 1%) 20 59 C3H3O 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (50.0 MHz, COCI, solution) proton coupied solvent proton decoupled 200 160 120 80 40 O 8 (ppm) 'H NMR Spectrum (200 MHz, COCI, solution) expansions TMS 4.5 4.0 1.5 1.0 ppm exchanges with Dz0 ppm 10 7 4 8 (ppm) yead oseg jo% Problem 14 IR Spectrum (iquid fim) 3354 4000 3000 2000 1600 1200 800 V (cm") 100 Mass Spectrum 45 80 No significant UV absorption above 220 nm M*- 60 (< 1%) 20 59 C3H3O 40 80 120 160 200 240 280 m/e 13C NMR Spectrum (50.0 MHz, COCI, solution) proton coupied solvent proton decoupled 200 160 120 80 40 O 8 (ppm) 'H NMR Spectrum (200 MHz, COCI, solution) expansions TMS 4.5 4.0 1.5 1.0 ppm exchanges with Dz0 ppm 10 7 4 8 (ppm) yead oseg jo%