Compound K, molecular formula C6H14O, readily undergoes acid-catalyzed dehydration when warmed with phosphoric acid to give compound L, molecular formula C6H12, as the major organic product. The 1H-NMR spectrum of compound K shows signals at d 0.90 (t, 6H), 1.12 (s, 3H), 1.38 (s, 1H), and 1.48 (q, 4H). The 13C-NMR spectrum of compound K shows signals at d 72.98, 33.72, 25.85, and 8.16. Deduce the structural formulas of compounds K and L.

Compound K, molecular formula C6H14O, readily undergoes acid-catalyzed dehydration when warmed with phosphoric acid to give compound L, molecular formula C6H12, as the major organic product. The 1H-NMR spectrum of compound K shows signals at d 0.90 (t, 6H), 1.12 (s, 3H), 1.38 (s, 1H), and 1.48 (q, 4H). The 13C-NMR spectrum of compound K shows signals at d 72.98, 33.72, 25.85, and 8.16. Deduce the structural formulas of compounds K and L.

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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