When 2-bromo-3,3-dimethylbutane is treated with K+ −OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3dimethylbutan-2-ol is treated with H2SO4, the major product U has the same molecular formula. Given the following 1H NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1H NMR of U: 1.60 (singlet) ppm

When 2-bromo-3,3-dimethylbutane is treated with K+ −OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3dimethylbutan-2-ol is treated with H2SO4, the major product U has the same molecular formula. Given the following 1H NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1H NMR of U: 1.60 (singlet) ppm

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 53AP: Treatment of 3,4-dibromohexane with strong base leads to loss of 2 equivalents of HBr and formation...

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When 2-bromo-3,3-dimethylbutane is treated with K+ −OC(CH3)3, a singleproduct T having molecular formula C6H12 is formed. When 3,3-dimethylbutan-2-ol is treated with H2SO4, the major product U has thesame molecular formula. Given the following 1H NMR data, what are thestructures of T and U? Explain in detail the splitting patterns observedfor the three split signals in T.1H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet ofdoublets, 1 H, J = 18, 10 Hz) ppm1H NMR of U: 1.60 (singlet) ppm Additional problems on the spectroscopy of alkenes are given in Chapters A–C:Mass spectrometry: A.16b, A.20, A.23Infrared spectroscopy: B.5, B.7(A), B.12c, B17a, B.18cNuclear magnetic resonance spectroscopy: C.12a; C.15d, e; C.29d; C.32d;C.37; C.38d, f; C.43i, j; C.44; C.45; C.49d, f; C.50b; C.51c; C.55
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