Chapter 23, Problem 33P

Treatment of $\text{2,4,6-tri-tert-butylphenol}$ with bromine in cold acetic acid gives the

compound ${\text{C}}_{\text{18}}{\text{H}}_{\text{29}}\text{BrO}$ in quantitative yield. The infrared spectrum of this compound

contains absorptions at $\text{1630}$ and $\text{1655}$ ${\text{cm}}^{\text{-1}}$. Its ${}^{\text{1}}\text{H}$ NMR spectrum shows only three peaks

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

the compound?