Your team is faced with a puzzle. Four isomeric compounds, A – D, with the molecular formula C₄H₉BrO react with KOH to produce E – G with the molecular formula C₄H₈O. Molecules A and B yield compounds E and F, respectively. The NMR spectra of compounds C and D are identical, and both furnish the same product, G. Although some of the starting materials are optically active, none of the products is. Moreover, each of E, F, and G displays only two ¹H NMR signals of varying chemical shifts, none of them located between δ 4.6 and 5.7 ppm. Both the respective resonances of E and G are complex, whereas F exhibits two singlets. Proton-decoupled ¹³C NMR spectra for E and G show only two peaks, whereas F exhibits three. Using this spectral information, work together to determine which isomers of C₄H₉BrO will yield the respective isomers of C₄H₈O. When you have matched reactant and product, divide the task of predicting the proton and carbon NMR spectra of E, F, and G among yourselves. Estimate the ¹H and ¹³C chemical shifts for all, and predict the respective DEPT spectra.