Question

Provide complete interpretation for all spectra and suggest a structure flr each compound

Answer 1

Identification of compound

IR

3300 cm-1 broad peak for O-H stretch

3000-3100 cm-1 for sp2 =C-H stretch

2850-2950 cm-1 for aliphatic -C-H stretch

1620 cm-1 peak for C=C stretch

1H NMR

2.6 ppm (triplet, 2H) for CH2 between Ph and CH2

3.6 ppm (triplet, 2H) for CH2 between CH2 and OH

4.1 ppm (singlet, 1H) for OH proton

7.1 ppm (singlet, 5H) for Ph protons

13C NMR

44.6 ppm, 68.5 ppm for the teo CH2's

the other four peaks are for aromatic carbons

Mass

122 M+

91 by loss of CH2CH2OH

45 for fragment CH2CH2OH

Structure would be thus,

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