ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
12th Edition
ISBN: 9781119766919
Author: Solomons
Publisher: WILEY
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Chapter 10, Problem 41P

Hydrogen peroxide and ferrous sulfate react to produce hydroxyl radical (HO·), as reported in 1894 by. English chemist H.J. H. Fenton. When tert-butyl alcohol is treated with HO· generated this way, it affords a crystalline reaction produa X, mp 92 °C, which has these spectral properties:

MS: heaviest mass peak is at m/z 131

IR: 3620, 3350 (broad), 2980, 2940, 1385, 1370 cm−1

1 H NMR: sharp singlets at δ 1.22, 1.58, and 2.95 (6:2: 1 area ratio)

1 3 C NMR: δ 28 ( C H 3 ) ,   35 ( C H 2 ) ,   68 ( C )

Draw the structure of X and write a mechanism for its formation.

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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10
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