CHM 2260 Organic Chemistry Laboratory Analytical Data Sheet for Experiment 5 (Al

Question

CHM 2260 Organic Chemistry Laboratory Analytical Data Sheet for Experiment 5 (Aldol condensation) Structure Yield|g and % 1,5-Diphenyl-1,4- pentadien-3-one Formula TLC R value Molar Mass [&/mol] TLC eluant Color and Form Melting Point H NMR (300 MHz, solvent coa) [ppm) l multiplicity! #Of H | NMR (300 MHz, solvent-CDC.) [Pprn] __ Peak assign Peak assign. MS FT-IR (NaCI plate, thin film) m/2 | % relative lon assignment Wavenumber Bond assignment intensity(structure of ion) 234 3047 and 3020 131 1671

Explanation / Answer

Spectral prediction

compound : 1,5-diphenyl-1,4-pentanedien-3-one

1H NMR

2 and a : 6.6 ppm (doublet, 2H)

3 and b : 6.8 ppm (doublet, 2H)

5 and c : 7.2 ppm (doublet, 4H)

6 and d : 7.0 ppm (triplet, 4H)

7 and e : 7.6 ppm (triplet, 2H)

13C NMR

1 : 205 ppm

2 and a : 105 ppm

3 and b : 110 ppm

4 : 138 ppm

5 and c : 128 ppm

6 and d : 125 ppm

7 and e : 130 ppm

IR

3060 cm-1 for sp2 =C-H stretch

1710 cm-1 for C=O stretch

1500-1600 cm-1 peaks for C=C of aromatic

1630 cm-1 for C=C alkene

1445 cm-1 for C-O stretch

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