Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
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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