An unknown compound A is a liquid, bp 141 degree C. The MS shows a molecular ion

Question

An unknown compound A is a liquid, bp 141 degree C. The MS shows a molecular ion at 74 m/z. Other important peaks found in the MS spectrum are: 57 and 29 m/z. The IR spectrum revealed frequencies (cm^-1) at 3500 - 2800 (broad), 3000, 1705, 1465, 1375, 1150. Compound A is soluble in water and aqueous KHCO_3 based on the solubility tests. Propose a structure for compound A that matches your spectral interpretation. Briefly, provide a short narrative to describe the rationale behind your propose structure.

Explanation / Answer

Compound A

IR

2800-3500 cm-1 for O-H of carboxylic acid

1705 cm-1 for C=O stretch

3000 cm-1 for aliphatic C-H stretch

1465 cm-1 for C-O stretch

MS

M+ 74

m/z 57 by loss of -OH

m/z 29 by loss of CO

Possible structure

CH3-CH2-COOH

Propionic acid

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