Question

Provide a structure for the following compound: C9H10O3; IR: 2400–3200, 1700, 1630 cm–1; 1H NMR: δ 1.53 (3H, t, J = 8 Hz); δ 4.32 (2H, q, J = 8 Hz); δ 7.08, δ 8.13 (4H, pair of leaning doublets, J = 10 Hz); δ 10 (1H, broad, disappears with D2O shake)

Answer 1

Answer:

The answer is Ethyl 3-hydroxybenzoate (structure attached).

Explanation:

The following can be elucidated from IR table of values:

2400- 3200 cm-1 ⇒ Carboxylic acid

17000 cm-1 ⇒ C=O bond (aldehyde, ketone)

1630 cm-1 ⇒ C=C (alkene) or aromatics

H NMR values:

1.53 ⇒ CH3 next to an electronegative, hence the high chemical shift (deshielded)

4.32⇒CH2 next to a CH3 and an R group (possible deshielding)

7.08, 8.13 ⇒ aromatics.

The structure is attached.