AdbuCCDUL Normal No Spacing Heading 1 c Chemistry Lab noevenagel Condensation re

Question

AdbuCCDUL Normal No Spacing Heading 1 c Chemistry Lab noevenagel Condensation reaction ab Questions cussion of the synthesis and isolation of your coumarin product including, 1· the calculated percent yield of your coumarin product and comments on its purity based on the literature melting point and literature IR spectrum. Label all major peaks of the IR spectrum of your final product, specifying the absorptions associated with the carbon-carbon double bond and the carboxylic ester functions. In the attached 'H NMR spectrum of ethyl-3-coumarincarboxylate, assign the various resonances (peaks) to the hydrogen nuclei responsible for them.

Explanation / Answer

Spectral analysis of coumarin product

1H NMR

1.44 ppm (t, 3H) for CH3 next to CH2

4.45 ppm (q, 2H) for CH2 between CH3 and oxygen

7.46 ppm (t, 1H) for aromatic proton

7.48 ppm (d, 1H) for aromatic proton

7.63 ppm (t, 1H) for aromatic proton

7.7 ppm (d, 1H) for aromatic proton

8.53 ppm (s, 1H) for alkenic proton

IR

3062 cm-1 for sp2 =C-H stretch

2877 and 2912 cm-1 for sp3 -C-H stretch

1604 cm-1 for C=C stretch

1448 cm-1 for C-O stretch

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