Compounds W and X are isomers. They have the molecular formula C9H8O. The IR spectrum of each compound shows a strong absorption band near 1715 cm−1. Oxidation of either compound with hot, basic potassium permanganate followed by acidification yields phthalic acid. The proton NMR spectrum of W shows a multiplet at δ 7.3 and a singlet at δ 3.4. The proton NMR spectrum of X shows a multiplet at δ 7.5, a triplet at δ 3.1, and a triplet at δ 2.5. Propose structures for W and X.

Compounds W and X are isomers. They have the molecular formula C9H8O. The IR spectrum of each compound shows a strong absorption band near 1715 cm−1. Oxidation of either compound with hot, basic potassium permanganate followed by acidification yields phthalic acid. The proton NMR spectrum of W shows a multiplet at δ 7.3 and a singlet at δ 3.4. The proton NMR spectrum of X shows a multiplet at δ 7.5, a triplet at δ 3.1, and a triplet at δ 2.5. Propose structures for W and X.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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