Question

Propose a suitable chemical structure of the organic compounds using the following NMR data and molecular formula

(1) Molecular formula : C₁₀H₁₄

¹H (d) ppm : 3H doublet (1.2), 1H sextet (2.5), 2H quintet (1.6), 3H triplet (0.8) and 5H singlet (7.27)

(2) Molecular formula : C₉H₁₂

¹H (d) ppm : 6H doublet (1.3), 1H septet (3.2), 5H singlet (7.27).​​​

Answer 1

(1) Double bond equivalent of C₁₀H₁₄ = 4

5 H_a = 7.27 ppm (singlet)

1 H_b = 2.5 ppm (sextet)

3 H_c = 1.2 ppm (doublet)

2 H_d = 1.6 ppm (quintet)

3 H_e = 0.8 ppm (triplet)

(2) Double bond equivalent of C₉H₁₂ = 4

6 H_a = 1.3 (doublet)

1 H_b = 3.2 (septet)

5 H_c = 7.27 (singlet)