Question

I have read and followed the above requirements for this project. Degree of Unsaturation Draw the structure of your compound and indicate the ppm of each of the M's. Degree of Unsaturation Draw the structure of your compound and indicate the ppm of each of the M's.
Can someone help me with these NMR questions?

Answer 1

Double bond equivalent for

C_aH_bO_cN_dX_e = a+1 - (b/2) - (d/2) + e/2

1.

Double bond equivalent for C₅H₉BrO₂

C₅H₉BrO₂ = 5 + 1 - (9/2) + (1/2) = 6 - 5 = 1

¹³C = 5 peaks

$\Rightarrow$ 5 different types of carbon.

¹H NMR

0.95 (t, 3H) - So, CH3 group and near a CH2 group present.

1.72 (m, 2H) - So, CH2 group and near more alkyl group present.

3.85 (s, 2H) - So, CH2 group with no adjacent carbon bearing hydrogen and Br group present (EWG)

4.15 (t, 2H) - So, CH2 group and near a CH2 group present. But it is at 4.15 ppm so, -COO group adjacent to it. The structure is shown in figure.

2.

C₈H₈O₂ = 8 + 1 - (8/2) = 9 - 4 = 5

So, 5 double bond equivalent. 4 double bond and 1 ring

¹³C = 8 peaks

$\Rightarrow$ 8 different types of carbon.

¹H NMR

3.98 (s, 3H) - So, CH3 group no nearby no carbon bearing hydrogens.

7.60 (m, 4H) - So, 4 aromatic protrons.

10.00 (s, 1H) - So, aldehydic protron. The structure is shown in figure.

0 4.15 0.5 385 1.72 2. 760 7.60 าย 760 0