Question

11. 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 product 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 'H NMR: sharp singlets at 8 1.22. 1.58, and 2.95 (6:2:1 area ratio) 13C NMR: 8 28 (CH3), 35 (CH2), 68 (C) Draw the structure of X. Show how you used each spectral information to deduce the structure. [1+1+1+1+1=5]

Answer 1

11 The 5tueluri Wi 내3 CH3 C- -CH CH2 c- OH HO CA3 dimerise MO no H Fyan MS data'.- feak z 2 13 CH2 CH3 CH3 2ć-c-CH2 CH-CH2-0H ch HO-CCH CH3 CH CH2 w/z키131 3 at 3620 Cn $4Yatelawg fre T IR Data OH dhe H-NMR au 13c-NMR are thyea Kind Theye aud ton Kinds C aloins HNMR 6H(S)1.5 d2525)-1.22 (S 2.75 th ree HOC CH2-CH2 C OH S 22 Scanned with CS CamScanner