A compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm-1 and

Question

A compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm-1 and shows a single absorp in the proton NMR spectrum at delta 3.00. When heated gently with methanol, compound B, C5H8O4, is obtained. Compound B has IR absorptions at 2500-3000 (broad), 1730, and 1701 cm-1, and its proton NMR spectrum in D2O consists of resonances at delta 2.7 (complex splitting) and delta 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry. The IR data indicate that compound A contains C=O and C-O groups, and compound B contains C=O and O-H groups. Methanol treatment generates only compound B; no sideproducts are involved. Recall that O-H protons are rapidly exchanged for deuterium when D2O is present, and that deuterium nuclei are "silent" in proton NMR. Check carefully that the B structure represents C5H8O4.

Explanation / Answer

B formula is C5H8O4 , 5 carbons , molecule can be CH3O-(C=O)-CH2-CH2--C(=O)OH . where two CH2 -CH2 protons will show complex peaks at 2.7 ppm

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