ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 23, Problem 33P

Treatment of 2,4,6-tri-tert-butylphenol with bromine in cold acetic acid gives the

compound C 18 H 29 BrO in quantitative yield. The infrared spectrum of this compound

contains absorptions at 1630 and 1655 cm -1 . Its 1 H NMR spectrum shows only three peaks

(all singlets), at δ 1 .2 , 1 .3 , and 6 .9 , in the ratio 9:18:2 . What is a reasonable structure for

the compound?

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