O Draw chemical structures from B to G to complete the following reaction scheme. The starting compound B shows three singlets in a 'H NMR experiment with chemical shifts of 3.72 ppm, 3.49 ppm, and 2.26 ppm using tetramethylsilane as an internal standard in deuterated chloroform. The respective ratio of integration is 3: 2:3. Furthermore, compound B is positive for the iodoform test. B C5H₂O3 HCI, H₂O E heat H3C CH3 1. CH₂O (1.0 equivalent) 2. CH3Br (1.0 equivalent) HCI, H₂O heat F LL OH™ C 12 (excess) H3O+ heat OH™ (excess) SOCI₂ CH3OH D G C4H8O2

O Draw chemical structures from B to G to complete the following reaction scheme. The starting compound B shows three singlets in a 'H NMR experiment with chemical shifts of 3.72 ppm, 3.49 ppm, and 2.26 ppm using tetramethylsilane as an internal standard in deuterated chloroform. The respective ratio of integration is 3: 2:3. Furthermore, compound B is positive for the iodoform test. B C5H₂O3 HCI, H₂O E heat H3C CH3 1. CH₂O (1.0 equivalent) 2. CH3Br (1.0 equivalent) HCI, H₂O heat F LL OH™ C 12 (excess) H3O+ heat OH™ (excess) SOCI₂ CH3OH D G C4H8O2

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.8: More Complex Spin–spin Splitting Patterns

Problem 15P: 3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled...

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