tert-Butyl esters [RCO2C(CH3)3] are converted into carboxylic acids (RCO2H) by reaction

Chapter 7, Problem 7.54

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tert-Butyl esters [RCO2C(CH3)3] are converted into carboxylic acids (RCO2H) by reaction with trifluoroacetic acid, a reaction useful in protein synthesis (Section 26.7). Assign E,Z designation to the double bonds of both reactant and product in the following scheme, and explain why there is an apparent change of double-bond stereochemistry: O O CF3CO2H H3C C H C OCH3 CC OC(CH3)3 O O H3C C H C OCH3 CC C(CH3) + H2C 2

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