Compound 1 and compound 2 both contain tritium (T), which is an isotope of hydrogen

Chapter 19, Problem 19.88

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Compound 1 and compound 2 both contain tritium (T), which is an isotope of hydrogen (tritium = 3 H). Both compounds are stable upon treatment with aqueous base. However, upon prolonged treatment with aqueous acid, compounds 1 and 2 both lose tritium, to give 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene, respectively (J. Am. Chem. Soc. 1967, 89, 44184424): 1 2 T OCH3 T OCH3 H3CO H3CO OCH3 (a) Draw a mechanism showing how tritium is removed from compounds 1 and 2. (b) Use your mechanism to predict which compound (1 or 2) is expected to lose tritium at a faster rate. Justify your answer.

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