Question

Draw the structure in the box 40) 7. Based on the spectral data shown, determine the structure of this compound. eo 60 20 1000 1500 200 po00 2000 40 20 140 160 40 120 180 60 100 m/z SH 2H Two 2H triplets Actually 3 peaks 140 160 12o 100

Answer 1

Hi Dear Friend, the unknown identified as benzyl 2-chloroethyl ether (IUPAC: 2-chloroethoxymethylbenzene )

IR:

3030 cm-1, medium, aromatic sp2 =C-H stretch

2950 & 2850 cm-1, strong, sp3 C-H stretch

1350 - 1450 cm-1, sp3 C-H bending

1100 cm-1, strong, ether C-O stretch

700 & 740 cm-1, strong, sp3 C-Cl stretch

Mass:

M+ (molecular ion) at m/z 170, in addition there is M+2 peak at m/z 172 - the intensity ratio of M+ : M+2 is 3:1 clearly indicates presence of Chlorine atom

base peak is at m/z 91

HNMR:

5H, multiplet in the aromatic region indicates mono-substituted benzene ring

2H, singlet at 4.6 ppm indicates a methylene group is in between phenyl ring and ether (Ph -CH₂-OR)

two 2H, triplets indicate -CH₂-CH₂-X environment

CNMR:
near 70 ppm indicate those carbons are attached to "O" atom

Assignments of HNMR & CNMR:

a HhHbHc H. * Assignment shift integration splitting Assignment shift Ha 1.3.7.4 5H multiplet 43 10. 4.6 2H singlet 3. 3.6 triplet 2H _2H ទននន? 73 138 127 128 127 triplet

Hope this helped you!

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