Question

Attach H-NMR (45 MHz) spectrum in CDCl and tabulate (as far as possible) the peak assignments below (10 pts): Shift range 8
4 13 12 11 10 9 8 7 15.32 127.50
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Answer #1

The given molecule is cis-1,2,3,6-Tetrahydrophthalic anhydride. This is well known studied molecule.

(IUPAC: (3aR,7aS)-3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione)

Shift ------------- splitting --------------- coupling (in Hz) ----------------- integration ----------------- Assignment

6.0 ppm -------- ddd ----------------------10.3, 2.4, 1.9 --------------------- 2H ------------------------------- HA

2.4 ppm -------- ddd ---------------------- 14.1, 9.8, 2.4 -------------------- 2H --------------------------------HB

2.3 ppm -------- ddd ---------------------- 14.1, 4.3, 1.9 -------------------- 2H --------------------------------HB'

3.8 ppm -------- ddd ------------------------ 9.8, 8.1, 4.3 -------------------- 2H --------------------------------HC

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