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)
To deduce the structure of the compound based on the given data, we need to analyze the information from the Infrared Spectroscopy (IR) and proton Nuclear Magnetic Resonance (1H NMR) spectra.
Starting with the IR spectrum, the absorption peaks at 2400-3200 cm-1 and 1700 cm-1 are indicative of the presence of two important functional groups: a broad peak in the 2400-3200 cm-1 range corresponds to an -OH (hydroxyl) group, while the peak at 1700 cm-1 corresponds to a carbonyl group, typically found in carboxylic acids, esters, or ketones.
Moving on to the 1H NMR spectrum, we find several signals that will help us identify the specific elements of the compound structure:
1. δ 1.53 (3H, t, J = 8 Hz): This is a triplet (t) peak at δ 1.53 ppm, with a coupling constant (J) of 8 Hz. This signal corresponds to a methyl group (CH3).
2. δ 4.32 (2H, q, J = 8 Hz): This is a quartet (q) peak at δ 4.32 ppm, with a coupling constant (J) of 8 Hz. This signal corresponds to a methylene group (CH2).
3. δ 7.08, δ 8.13 (4H, pair of leaning doublets, J = 10 Hz): These are two leaning doublets (dd), one at δ 7.08 ppm and the other at δ 8.13 ppm. Each of them represents two hydrogens (H) that are coupled with a coupling constant (J) of 10 Hz. These signals correspond to aromatic protons.
4. δ 10 (1H, broad, disappears with D2O shake): This broad signal at δ 10 ppm indicates the presence of an -OH (hydroxyl) group.
Based on the given information, we can deduce the following structure:
CH3 CH2
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CH3-CH2-CH(OH)-C6H4-COOH
This structure represents a compound with a hydroxyl group (-OH) attached to an alkyl chain (CH3-CH2-) which is connected to a phenyl group (C6H4-) carrying a carboxylic acid group (-COOH).